2-Methoxyphenylboronic acid → 6-Cyano-2'-methoxy-biphenyl-3-carboxylic acid methyl ester

HRID 1909019Notes

Reaction equation

HRID 1909019 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6](Br)[CH:5]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH3:14])[C:7]([C:10]#[N:11])=[CH:8][CH:9]=1)=[O:13]

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 23379143Methyl 3-bromo-4-cyanobenzoate

Product 1

HCID 672861136-Cyano-2'-methoxy-biphenyl-3-carboxylic acid methyl esterYield 74.8%

Procedure

By following procedures described in General procedure C (Suzuki), 3-bromo-4-cyano-benzoic acid methylester (0.205 g, 0.85 mmol) and 2-methoxy phenyl boronic acid (0.156 g, 1.02 mmol) were used to obtain the title compound (0.170 g, 62%), following SiO2 chromatography (hexanes/EtOAc=6:1). MS(ESI) m/z 268.0 (M+H)+

Sources & evidence

ORD record
ord-687d9a62e2b0439a98abbd5e406145e9
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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