5-Chloro-2-cyanophenylboronic acid → HCID 71536086, compound

HRID 1519361Notes

Reaction equation

HRID 1519361 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]=[CH:28][C:29]([C:35]#[N:36])=[C:30](B(O)O)[CH:31]=1>>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:35]#[N:36])=[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:27]=1

Participants

3

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 71536086HCID 71536086, compoundYield 12.4%

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 and 5-chloro-2-cyanophenylboronic acid (available from Combi-Blocks Inc.; 73 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 5′-chloro-2′-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (12 mg, 12%). 1H NMR (400 MHz, DMSO-d6) δ 13.38 (br s, 1H), 8.63 (d, J=2.0 Hz, 1H), 8.52 (s, 1H), 8.31-8.37 (m, 2H), 8.10 (dd, J=8.5, 2.0 Hz, 1H), 7.97 (d, J=8.3 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.65-7.73 (m, 2H), 7.59 (d, J=8.0 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-a46d4b87e6704148b3d5f4e37e55695f
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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