2,4-Bis(trifluoromethyl)phenylboronic acid → HCID 86679866, compound

HRID 1519373Notes

Reaction equation

HRID 1519373 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]([F:41])([F:40])[C:27]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=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:28]4[CH:29]=[CH:30][C:31]([C:33]([F:36])([F:34])[F:35])=[CH:32][C:27]=4[C:26]([F:25])([F:40])[F:41])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 27826672,4-Bis(trifluoromethyl)phenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679866HCID 86679866, compoundYield 5%

Procedure

Using the conditions of General Procedure A 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-bis(trifluoromethyl)phenylboronic acid (available from Combi-Blocks Inc.; 129 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′-bis-trifluoromethyl-biphenyl-2-carboxylic acid (7 mg, 5%). 1H NMR (300 MHz, DMSO-d6) δ 13.17 (br s, 1H), 8.62 (s, 1H), 8.50 (s, 1H), 8.27-8.37 (m, 2H), 8.05-8.15 (m, 3H), 7.77 (d, J=8.3 Hz, 1H), 7.64 (d, J=7.9 Hz, 1H), 7.48 (d, J=8.1 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-60ad7a4ed4f34c81bfafce9022b18cb5
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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