(3-Methoxyphenyl)boronic acid → HCID 71535533, compound

HRID 1519344Notes

Reaction equation

HRID 1519344 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:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1>>[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:31]4[CH:30]=[CH:29][CH:28]=[C:27]([O:26][CH3:25])[CH:32]=4)=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 71535533HCID 71535533, compoundYield 71.2%

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 3-methoxyphenylboronic acid (available from Combi-Blocks 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]-3′-methoxy-biphenyl-2-carboxylic acid (65 mg, 71%). 1H NMR (400 MHz, DMSO-d6) δ 13.15 (br s, 1H), 8.46 (s, 1H), 8.28-8.39 (m, 2H), 8.20 (d, J=7.8 Hz, 1H), 8.09 (dd, J=8.5, 1.8 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.36 (t, J=7.8 Hz, 1H), 6.86-7.06 (m, 3H), 3.80 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-d4bffb3b9fa9404ea31d7914118d8db6
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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