3-Cyanophenylboronic acid → HCID 86679854, compound

HRID 1519360Notes

Reaction equation

HRID 1519360 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.[C:25]([C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1)#[N:26]>>[C:25]([C:27]1[CH:32]=[C:31]([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:30]=[CH:29][CH:28]=1)#[N:26]

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679854HCID 86679854, compoundYield 21%

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-cyanophenylboronic acid (available from Combi-Blocks Inc.; 59 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 3′-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (19 mg, 21%). 1H NMR (400 MHz, DMSO-d6) δ 13.30 (br s, 1H), 8.48 (s, 1H), 8.45 (d, J=1.8 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.26 (dd, J=8.0, 1.8 Hz, 1H), 8.10 (dd, J=8.3, 2.0 Hz, 1H), 7.85-7.92 (m, 2H), 7.71-7.81 (m, 2H), 7.57-7.69 (m, 2H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-005ed07a6eec496685180701eab55910
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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