2,3,5-Trifluorophenylboronic Acid → HCID 86679872, compound

HRID 1519381Notes

Reaction equation

HRID 1519381 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][C:29]([F:33])=[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:27]4[CH:28]=[C:29]([F:33])[CH:30]=[C:31]([F:32])[C:26]=4[F:25])=[CH:6][CH:7]=3)[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 40788432,3,5-Trifluorophenylboronic AcidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679872HCID 86679872, compoundYield 24%

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 2,3,5-trifluorophenylboronic acid (available from Combi-Blocks Inc.; 70 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′,5′-trifluoro-biphenyl-2-carboxylic acid (23 mg, 24%). 1H NMR (400 MHz, DMSO-d6) δ 13.36 (br s, 1H), 8.55 (s, 1H), 8.50 (s, 1H), 8.28-8.39 (m, 2H), 8.10 (d, J=8.3 Hz, 1H), 7.77 (dd, J=8.4, 1.6 Hz, 1H), 7.54-7.66 (m, 2H), 7.22-7.28 (m, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-04b1c98d598e4b01916eec3378cff888
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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