(3-Chloro-4-cyanophenyl)boronic acid → HCID 86679856, compound

HRID 1519363Notes

Reaction equation

HRID 1519363 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:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:31]=1[C:32]#[N:33]>>[Cl:25][C:26]1[CH:27]=[C:28]([C:5]2[C:4]([C:3]([OH:2])=[O:24])=[CH:9][C:8]([C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=4)[N:14]=3)=[CH:7][CH:6]=2)[CH:29]=[CH:30][C:31]=1[C:32]#[N:33]

Participants

3

Reactant 2

HCID 46738932(3-Chloro-4-cyanophenyl)boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679856HCID 86679856, compoundYield 43.2%

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 and 3-chloro-4-cyanophenylboronic acid (available from Combi-Blocks Inc.; 73 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 3′-chloro-4′-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (42 mg, 43%). 1H NMR (400 MHz, DMSO-d6) δ 13.40 (br s, 1H) 8.44-8.55 (m, 2H), 8.34 (d, J=1.8 Hz, 1H), 8.28 (dd, J=8.0, 2.0 Hz, 1H), 8.07-8.13 (m, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.81 (d, J=1.3 Hz, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.56 (dd, J=8.0, 1.5 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-01451695342644e78feadfcb6ffc486b
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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