3-Chlorothiophene-2-boronic acid → HCID 86679883, compound

HRID 1519393Notes

Reaction equation

HRID 1519393 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:30]=[CH:29][S:28][C:27]=1B(O)O>>[Cl:25][C:26]1[CH:30]=[CH:29][S:28][C:27]=1[C:5]1[CH:6]=[CH:7][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:9][C:4]=1[C:3]([OH:2])=[O:24]

Participants

3

Reactant 2

HCID 193509333-Chlorothiophene-2-boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679883HCID 86679883, compoundYield 12%

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 3-chlorothiophene-2-boronic acid (available from Combi-Blocks Inc.; 81 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2-(3-Chloro-thiophen-2-yl)-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid (14 mg, 12%). 1H NMR (400 MHz, DMSO-d6) δ 13.23 (br s, 1H), 8.50 (s, 1H), 8.47 (d, J=2.0 Hz, 1H), 8.33 (d, J=2.0 Hz, 1H), 8.27 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.5, 2.0 Hz, 1H), 7.74-7.81 (m, 2H), 7.60 (d, J=8.0 Hz, 1H), 7.15 (d, J=5.3 Hz, 1H), 7.15 (d, J=5.3 Hz, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-c1506bb7b41e484fa3ce08b46b2df24e
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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