4-Methyl-3-thiopheneboronic acid → HCID 86679880, compound

HRID 1519390Notes

Reaction equation

HRID 1519390 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.[CH3:25][C:26]1[C:27](B(O)O)=[CH:28][S:29][CH:30]=1>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[N:14]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:27]4[C:26]([CH3:25])=[CH:30][S:29][CH:28]=4)=[C:4]([CH:9]=3)[C:3]([OH:2])=[O:24])[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

3

Reactant 2

HCID 50839314-Methyl-3-thiopheneboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679880HCID 86679880, compoundYield 55%

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 and 4-methyl-3-thiopheneboronic acid (available from Combi-Blocks Inc.; 57 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2-(4-methyl-thiophen-3-yl)-benzoic acid (49 mg, 55%). 1H NMR (400 MHz, DMSO-d6) δ 13.04 (br s, 1H), 8.47 (s, 1H), 8.41 (d, J=1.8 Hz, 1H), 8.33 (d, J=2.0 Hz, 1H), 8.20 (dd, J=8.0, 2.0 Hz, 1H), 8.09 (dd, J=8.3, 2.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.35 (d, J=3.3 Hz, 1H), 7.13-7.26 (m, 1H), 2.54 (s, 3H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-c23b13a819804810a04883ad00fdae23
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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