2-Methoxyphenylboronic acid → HCID 71535532, compound

HRID 1519345Notes

Reaction equation

HRID 1519345 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)[CH:7]=[CH:6][C:5]=1Br.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[N:14]=[C:10]([C:8]3[CH:9]=[C:4]([C:3]([OH:2])=[O:24])[C:5]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[O:26][CH3:25])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 71535532HCID 71535532, compoundYield 39.4%

Procedure

Using the conditions of General Procedure B for Suzuki Coupling and Hydrolysis in Parallel Mode, 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6; 89 mg, 0.2 mmol) was reacted with 2-methoxyphenylboronic acid (available from Frontier Scientific, Inc.; 61 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′-methoxy-biphenyl-2-carboxylic acid (36 mg, 39%). 1H NMR (400 MHz, DMSO-d6) δ 12.75 (br s, 1H), 8.45 (s, 1H), 8.31-8.37 (m, 2H), 8.21 (d, J=8.0 Hz, 1H), 8.09 (d, J=8.3 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.27 (d, J=7.5 Hz, 1H), 7.04 (d, J=7.3 Hz, 2H), 3.69 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-9e878f7d900646ec8db672c5a72454ad
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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