2-Chloro-5-methylphenylboronic Acid (contains varying amounts of Anhydride) → 2'-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5'-methyl-biphenyl-2-carboxylic acid

HRID 1519391Notes

Reaction equation

HRID 1519391 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.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=1B(O)O>>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=1[C:5]1[C:4]([C:3]([OH:2])=[O:24])=[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]=1

Participants

3

Reactant 2

HCID 177502352-Chloro-5-methylphenylboronic Acid (contains varying amounts of Anhydride)HCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 866798812'-Chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5'-methyl-biphenyl-2-carboxylic acidYield 50%

Procedure

Using the conditions of General Procedure C 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; 111 mg, 0.25 mmol) was reacted with 2-chloro-5-methylphenylboronic acid (available from Combi-Blocks Inc.; 85 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5′-methyl-biphenyl-2-carboxylic acid (59 mg, 50%). 1H NMR (400 MHz, DMSO-d6) δ 13.00 (br s, 3H), 8.51 (d, J=2.0 Hz, 1H), 8.48 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.27 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.19-7.24 (m, 1H), 7.18 (s, 1H), 2.34 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-8d13e0a26d3647c0b2e72d352ed3db6b
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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