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20th January 2015 @ 13:36

Reaction Scheme 

Experimental Procedure

JS 18-1 [Synthesis of 4-(5-chloro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)benzonitrile (JS 18-1)]  (240 mg, 0.945 mmol) was dissolved in toluene (6 mL) and then treated with 2-(2-chlorophenyl)ethanol (0.15 mL, 1.131 mmol). KOH (174 mg, 3.12 mmol) & 18-crown-6 (27 mg, 0.096 mmol) were then added and the mixture was allowed to stir for 1 hour. The reaction was monitored by TLC (100% EtOAc) and after 1 h the starting materials had been consumed. 

The mixture was cooled to room temperature before water (15 mL) was added. The phases were separated and the aqueous layer was washed with EtOAc (4 x 15 mL). The organic layer was then washed with water until the aqueous later became neutral. The combined organic layers were dried over Na2SO4 and filtered before removing solvents in vacuo to produce the crude product. The crude was purified using dry flash column chromatography (100% EtOAc) to yield the titled compound as a white solid ( 271 mg, 0.723 mmol, 76.5% yield). 

SMILES 

ClC(C=CC=C1)=C1CCOC2=CC=CC3=NN=C(C4=CC=C(C#N)C=C4)N32

to

ClC(C=CC=C1)=C1CCOC2=CC=CC3=NN=C(C4=CC=C(C#N)C=C4)N32

InChI Strings 

InChI=1S/C21H15ClN4O/c22-18-5-2-1-4-16(18)12-13-27-20-7-3-6-19-24-25-21(26(19)20)17-10-8-15(14-23)9-11-17/h1-11H,12-13H2

to

InChI=1S/C21H15ClN4O/c22-18-5-2-1-4-16(18)12-13-27-20-7-3-6-19-24-25-21(26(19)20)17-10-8-15(14-23)9-11-17/h1-11H,12-13H2

TLC 

JS 19-1 TLC.JPG

NMR

JS 19-1 C.png

JS 19-1.png

Attached Files
15th January 2015 @ 04:26

GitHub Issue #277 and #278

See also: Synthesis of methyl 2-methoxy-2-phenylacetate (AEW 184-2)

AEW 216-1 (1 g, 6.02 mmol, 1 equiv.) was dissolved in DMF (12 mL) under Ar. Cs2CO3 (1.96 g, 6.02 mmol, 1 equiv.) was added and the reaction mixture was stirred at room temperature for 10 minutes. MeI (0.4 mL, 6.62 mmol, 1.1 equiv.) was then added and the reaction stirred at room temperature overnight. 

Data:


Hazard and Risk Assessment:

See: Synthesis of methyl 2-methoxy-2-phenylacetate (AEW 184-1)

InChi:

InChI=1S/C9H10O3/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8,10H,1H3/t8-/m0/s1

to

InChI=1S/C10H12O3/c1-12-9(10(11)13-2)8-6-4-3-5-7-8/h3-7,9H,1-2H3

O=C(OC)[C@H](C1=CC=CC=C1)O

to

O=C(OC)[C@H](C1=CC=CC=C1)OC


Attached Files
15th January 2015 @ 04:08

See also:Synthesis of methyl 2-methoxy-2-phenylacetate (AEW 184-1)

AEW 173-3 (3.0 g, 18.1 mmol, 1 equiv.) was dissolved in DMF (36 mL) under Ar. Cs2CO3 (5.9 g, 18.1 mmol, 1 equiv.) was added and the reaction mixture was stirred at room temperature for 10 minutes. MeI (2.28 mL, 19.9 mmol, 1.1 equiv.) was then added and the reaction stirred at room temperature overnight.


Hazard and Risk Assessent:

See: See also:Synthesis of methyl 2-methoxy-2-phenylacetate (AEW 184-1)

 

InChi:

InChI=1S/C9H10O3/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8,10H,1H3

to

InChI=1S/C10H12O3/c1-12-9(10(11)13-2)8-6-4-3-5-7-8/h3-7,9H,1-2H3


References:

DOI: 10.1016/S0040-4039(99)00083-0

Tetrahedron LettersVolume 40, Issue 10, 5 March 1999, Pages 1843–1846


Linked Posts
15th January 2015 @ 03:25

GitHub Issue #276 and #275 previously (#235 and #236)

See related attempts: Synthesis of methyl 2-(3,4-difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)acetate (AEW 109-1) and Synthesis of methyl 2-(3,4-difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)acetate (AEW 109-2)

Procedure:

AEW 173-1 (2 g, 12.0 mmol, 1 equiv.) and DHP (1.86 mL, 1.72 g, 20.4 mmol, 1.7 equiv.) were dissolved in anhydrous CH2Cl2 (8.5 mL) under Argon (NB exotherm so placed quickly in ice bath, in future cool befroe addition of DHP) and cooled to 0 ˚C. PPTS (74 mg, 0.30 mmol, 0.03 eq.) was added and the reaction mixture was stirred at 0 ˚C for 3 h (black solution) and then at rt for 20 h. 

CH2Cl2 (80 mL) was added and the resulting solution was shaken with portions of ice-cold water (3 x 10 mL) and once with saturated NaHCO(10 mL). The organic phase was dried (MgSO4) and filtered, and the solvent was removed under reduced pressure.

 

Hazard and Risk Assessment:

Reference:

New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-,Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands
Peter Huszthy, Masatoshi Oue, Jerald S. Bradshaw, Cheng Y. Zhu, Ting

J. Org. Chem., Vol. 57, No. 20, 1992 5383-5394

http://pubs.acs.org/doi/pdf/10.1021/jo00046a020?source=chemport

Attached Files
14th January 2015 @ 05:28

GitHub Isuue #275


Crude AEW 217-1 (~6.92 mmol) was dissolved in CH2Cl2 (60 mL) (orange/brown solution) and PIDA (2.23 g, 6.92 mmol, 1 equiv.) was added and the reaction mixture stirred at room temperature for 1h20. TLC shows new lower spot corresponding with Rf and bright violet of previous cyclised products - still trace of SM so sitrred for a further 20 min. TLC = complete.

The reaction was stopped and the organic layer washed with saturated NaHCO3 solution (30 mL x 2). The inorganic layer was extracted with CH2Cl2 (3 x 20 mL). The combined organic layers were dried (MgSO4), filtered and evaporated to yield

 

Hazard and Risk Assessement:

HIRAC AEW 218-1.pdf
 

Strings:

InChI=1S/C7H9ClN4/c1-2-3-10-12-7-5-9-4-6(8)11-7/h3-5H,2H2,1H3,(H,11,12)/b10-3+

to

InChI=1S/C7H7ClN4/c1-2-6-10-11-7-4-9-3-5(8)12(6)7/h3-4H,2H2,1H3

 

ClC1=CN=CC(N/N=C/CC)=N1

to

ClC1=CN=CC2=NN=C(CC)N21

Linked Posts
Attached Files