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12th March 2015 @ 20:43

Resynthesis of SGS 4-1. 

SGS 1-2 (crude, 1.007 g, 7.1 mmol) was stirred into MeCN (12 ml). 3-Pyridinecarboxaldehyde (0.74 g, 6.9 mmol, density 1.137 g/mL) was added and the reaction mixture (light brown suspension) was observed. The reaction mixture was stirred at room temperature for 7 days. 

29th January 2015 @ 16:10

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)]  (200 mg, 0.788 mmol) was dissolved in toluene (5.5 mL) and then treated with phenylethyl alcohol (0.12 mL, 0.95 mmol). KOH (145 mg, 2.6 mmol) & 18-crown-6 (24 mg, 0.078 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 not fully been consumed. Stirring for a further two hours showed that product had formed but starting material was still present 

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 (100/00 --> 00/100 Hexane/EtOAc) to yield the titled compound as a white solid ( 94 mg, 0.27 mmol, 34.6% yield). 

SMILES 

1. ClC1=CC=CC2=NN=C(C3=CC=C(C#N)C=C3)N21

to

2. N#CC(C=C1)=CC=C1C2=NN=C3C=CC=C(OCCC4=CC=CC=C4)N32

InChI Strings 

1. InChI=1S/C13H7ClN4/c14-11-2-1-3-12-16-17-13(18(11)12)10-6-4-9(8-15)5-7-10/h1-7H

to

2. InChI=1S/C21H16N4O/c22-15-17-9-11-18(12-10-17)21-24-23-19-7-4-8-20(25(19)21)26-14-13-16-5-2-1-3-6-16/h1-12H,13-14H2

NMR

JS 20-1 MeOH.png

Attached Files
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


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