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25th August 2016 @ 06:28

Procedure

HM7-1(80 mg, 339.39µmol, 1.0 equiv.), potassium hydroxide (66.65mg, 1.19mmol, 3.5 equiv.) and 18-crown-6 (6.28mg, 23.76µmol, 0.07 equiv.) were stirred in toluene (5 mL) and AEW alcohol (59.04mg, 373.33µmol, 1.1 equiv.) was added and the reaction mixture stirred at rt for 30 mins.


Water (20 mL) was added and the mixture was extracted with EtOAc (3 x 40 mL). Combined organic layers were washed with water (20 mL), brine (20 mL), dried (MgSO4) filtered and evaporated then purified by flash column chromatography using the Biotage IsoleraTM

Log

25th Aug

The reaction started at 4:00pm and left under room temperature overnight.

26th Aug

TLC was performed (75% EtOAc in petroleum) showing that the reaction has yet gone completion. Warm up. 

 

HIRAC

HM 8-1.docx

String

from

InChI=1S/C12H14ClN3/c13-9-5-4-6-10-11(9)12(15-14-10)16-7-2-1-3-8-16/h4-6,11H,1-3,7-8H2

and

InChI=1S/C8H8F2O/c9-7-2-1-6(3-4-11)5-8(7)10/h1-2,5,11H,3-4H2

to

InChI=1S/C20H21F2N3O/c21-15-8-7-14(13-16(15)22)9-12-26-18-6-4-5-17-19(18)20(24-23-17)25-10-2-1-3-11-25/h4-8,13,19H,1-3,9-12H2

Attached Files
24th August 2016 @ 04:31

 

Procedure

AEW 309-1 (~4.95 mmol, 1.00 equiv.) was dissolved in anhydrous diethyl ether (50 mL) and cooled to 0 ˚C. LiAlH4 (1 M in THF, 3.17 mL, 4.17 mmol, 0.64 equiv.) was added dropwise and the reaction mixture stirred for ten mins at 0 ˚C and then allowed to reach RT whilst stirring o/n.

 ice bath. Acetone added dropwise to quench excess LAH and then a saturated soln of Rochelle's salt was added (dropwise at start then with pouring, 80 mL). Stirred at 0 ˚C and then rt overnight. Work up: Ether extraction of aqueous, then acidified aqueous to pH 5. Extracted with ether (x2), dried combined organic layers (MgSO4), filtered and evaporated to give a crude yellow liquid (1.34 g, 5.67 mmol, 109% yield) dried further at highvac prior to NMR.

Data:

Crude NMR

AEW 311-1 crude.png
AEW 311-1 crude.jcamp
AEW 311-1 crude.mnova
AEW 311-1 crude.zip

Strings

InChI=1S/C10H10F2O3/c1-14-9(10(13)15-2)6-3-4-7(11)8(12)5-6/h3-5,9H,1-2H3

to

InChI=1S/C9H10F2O2/c1-13-9(5-12)6-2-3-7(10)8(11)4-6/h2-4,9,12H,5H2,1H3

O=C(OC)C(OC)C1=CC(F)=C(F)C=C1

to

OCC(OC)C1=CC(F)=C(F)C=C1

Attached Files
24th August 2016 @ 01:49

Procedure

The ratio between the reactants in this flask was as follows:50mg of 3-bromo-5-chloro-[1,2,4]triazolo[4,3-a]pyrazine(214µmol,1equiv.),6.16mg of Pd(dba)2(21.42µmol, 0.05equiv.), 33.21mg of Pd(dba)2(10.71µmol, 0.05equiv.) 36.90mg of piperazine (428.35µmol, 1.2equiv),30.87mg of t-BuONa(642.53µmol, 1.5equiv.),4.47mg of JohnPhos(14.99µmol,0.07equiv.) The reactants were placed in the flask and purged with argon then 2ml of toluene was added.The mixture was purged with argon again and stirred under argon at room temperature.The reaction will be monitored by TLC

 

HIRAC

HM 6-3.docx


Log

24th Aug

The reaction started at 3:10pm.After an hour, the reaction had gone completion.

TLC was perfomed(25%EtOAc in petroleum)

It looked like ,the product could be the base line spot


Attached Files
24th August 2016 @ 01:46

Procedure

The ratio between the reactants in this flask was as follows:250mg of 3-bromo-5-chloro-[1,2,4]triazolo[4,3-a]pyrazine(1.07mmol,1equiv.),30.79mg of Pd(dba)2(53.54µmol, 0.05equiv.), 33.21mg of Pd(dba)2(10.71µmol, 0.05equiv.) 109.42mg of piperadine (1.29mmol,126.94mml,  1.2equiv),154.37mg of t-BuONa(1.61mmol, 1.5equiv.),46.68mg of BINAP(74.96µmol,0.07equiv.) The reactants were placed in the flask and purged with argon then 2ml of toluene was added.The mixture was purged with argon again and stirred under argon at room temperature.The reaction will be monitored by TLC

Log

24th Aug

The reaction started at 3:20pm. After an hour, the reaction had almost gone completion according to TLC(25%of EtOAc in petroleum) There was still a small amout of SM so the reaction was left overnight.

25th Aug

The reaction mixure was diluted with 50ml of EtOAc and washed with 10ml of water. The aquaous layer was washed with EtOAc(2x15ml). And the oganic was conbined and concentrated (After working up, TLC looks different)then columned to yield 109mg orange powder. (Yield :43%)

 

 

 

HIRAC

HM 7-1.docx
Attached Files
23rd August 2016 @ 10:13

 

AEW 281-2 (~24.1 mmol, 1.00 equiv.) was dissolved in anhydrous diethyl ether (250 mL) and cooled to 0 ˚C. LiAlH4 (1 M in THF, 15.4 mL, 15.4 mmol, 0.64 equiv.) was added dropwise and the reaction mixture stirred for ten mins at 0 ˚C and then allowed to reach RT whilst stirring o/n.

 ice bath. Acetone added dropwise to quench excess LAH and then a saturated soln of Rochelle's salt was added (dropwise at start then with pouring, 80 mL). Stirred at 0 ˚C and then rt overnight. Work up: Ether extraction of aqueous, then acidified aqueous to pH 5. Extracted with ether (x2), dried combined organic layers (MgSO4), filtered and evaporated to give a crude yellow liquid (1.34 g, 5.67 mmol, 109% yield) dried further at highvac prior to NMR.


Data:

AEW 287-1 50% EtOAc.png

AEW 287-1.png
AEW 287-1.dx
AEW 287-1.zip

Strings:

InChI=1S/C16H22O4/c1-2-18-16(17)14(13-8-4-3-5-9-13)12-20-15-10-6-7-11-19-15/h3-5,8-9,14-15H,2,6-7,10-12H2,1H3

to

InChI=1S/C14H20O3/c15-10-13(12-6-2-1-3-7-12)11-17-14-8-4-5-9-16-14/h1-3,6-7,13-15H,4-5,8-11H2

O=C(OCC)C(COC1OCCCC1)C2=CC=CC=C2

to

OCC(COC1OCCCC1)C2=CC=CC=C2