(2,3-Difluorophenyl)boronic acid → HCID 86679877, compound

HRID 1519387Notes

Reaction equation

HRID 1519387 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.[F:25][C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[N:14]=[C:10]([C:8]3[CH:9]=[C:4]([C:3]([OH:2])=[O:24])[C:5]([C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([F:25])[C:31]=4[F:32])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 2734333(2,3-Difluorophenyl)boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679877HCID 86679877, compoundYield 69.2%

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 2,3-difluorophenylboronic acid (available from Combi-Blocks Inc.; 63 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′,3′-difluoro-biphenyl-2-carboxylic acid (64 mg, 69%). 1H NMR (400 MHz, DMSO-d6) δ 13.26 (br s, 1H), 8.52 (s, 1H), 8.50 (d, J=1.5 Hz, 1H), 8.34 (s, 1H), 8.31 (d, J=8.0 Hz, 1H), 8.10 (d, J=8.5 Hz, 1H), 7.74-7.81 (m, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.42-7.53 (m, 1H), 7.19-7.36 (m, 2H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-624fe87fda95410494ee616c3eed2f4a
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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