2,4-Difluorophenylboronic acid → HCID 86679871, compound

HRID 1519380Notes

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[CH:31]=[C:30]([F:32])[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:29]4[CH:28]=[CH:27][C:26]([F:25])=[CH:31][C:30]=4[F:32])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

Reactant 2

HCID 27343342,4-Difluorophenylboronic acid

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

Product 1

HCID 86679871HCID 86679871, compoundYield 17%

Procedure

Using the conditions of General Procedure C 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; 111 mg, 0.25 mmol) was reacted with 2,4-difluorophenylboronic acid (available from Frontier Scientific, Inc.; 79 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2′,4′-difluoro-biphenyl-2-carboxylic acid (19 mg, 17%). 1H NMR (400 MHz, DMSO-d6) δ 13.17 (br s, 1H), 8.46-8.52 (m, 2H), 8.33 (d, J=2.0 Hz, 1H), 8.26-8.31 (m, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.44-7.52 (m, 1H), 7.27-7.36 (m, 1H), 7.15-7.24 (m, 1H).

Workup

customthe acid was purified

Sources & evidence

ORD record: ord-faa8763405394f6bb170a322ca64830a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073881B2

Reaction notes

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