2-Chloro-5-fluorobenzeneboronic acid → HCID 74221632, compound

HRID 1519378Notes

Reaction equation

HRID 1519378 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.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1B(O)O>>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[C:5]1[C:4]([C:3]([OH:2])=[O:24])=[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]=1

Participants

3

Reactant 2

HCID 226481162-Chloro-5-fluorobenzeneboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 74221632HCID 74221632, compoundYield 10%

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-chloro-5-fluorophenylboronic acid (available from Combi-Blocks Inc.; 87 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-chloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-5′-fluoro-biphenyl-2-carboxylic acid (12 mg, 10%). 1H NMR (300 MHz, DMSO-d6) δ 13.14 (br s, 1H), 8.55 (d, J=1.7 Hz, 1H), 8.49 (s, 1H), 8.34 (d, J=1.9 Hz, 1H), 8.29 (dd, J=8.1, 1.9 Hz, 1H), 8.09 (dd, J=8.5, 2.1 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.56 (dd, J=8.6, 5.7 Hz, 1H), 7.48 (d, J=8.1 Hz, 1H), 7.30 (d, J=8.7 Hz, 2H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-1c8307defe5149dda04c145589a1a27d
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

Loading…