(4-Chloro-3-cyanophenyl)boronic acid → 4'-Chloro-3'-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid

HRID 1519364Notes

Reaction equation

HRID 1519364 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](B(O)O)=[CH:28][C:27]=1[C:35]#[N:36]>>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([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:28][C:27]=1[C:35]#[N:36]

Participants

3

Reactant 2

HCID 44119831(4-Chloro-3-cyanophenyl)boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 866798574'-Chloro-3'-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acidYield 19%

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 4-chloro-3-cyanophenylboronic acid (available from Combi-Blocks Inc.; 73 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4′-chloro-3′-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (18 mg, 19%). 1H NMR (400 MHz, DMSO-d6) δ 13.35 (br s, 1H), 8.44-8.51 (m, 2H), 8.34 (d, J=2.0 Hz, 1H), 8.28 (dd, J=8.0, 1.8 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 8.06 (d, J=2.3 Hz, 1H), 7.82 (d, J=8.5 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.74 (dd, J=8.5, 2.3 Hz, 1H), 7.61 (d, J=8.0 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-ac93484a29f8463d92a442af26df791e
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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