Dimethylformamide → 6-(Benzenesulphonylmethyl)-3-cyano-2-methoxybenzoic acid

HRID 2177673Notes

Reaction equation

[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:20][CH3:21])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][N:24](C=O)C>COC(C)(C)C.[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:20][CH3:21])[C:14]([C:23]#[N:24])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid (Example 7, 0.1 g), zinc cyanide (0.036 g) and tetrakis-(triphenylphosphine) palladium (0.015 g) in DMF was stirred and heated in the microwave at 180° C. for 10 minutes. After cooling, the mixture was diluted with t-butyl methyl ether, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by preparative HPLC (C18), eluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 35-98% to give 6-(benzenesulphonylmethyl)-3-cyano-2-methoxybenzoic acid (0.02 g) as a white solid.

Workup

temperatureAfter cooling
dry with materialdried (MgSO4)
filtrationfiltered
customThe filtrate was evaporated to dryness
customthe residue was purified by preparative HPLC (C18)
washeluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 35-98%

Sources & evidence

ORD record: ord-2b88a298236244228abab729988c82af
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

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