2,3,5-Trichlorophenylboronic acid → HCID 86679886, compound

HRID 1519396Notes

Reaction equation

HRID 1519396 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[C:31]([Cl:32])=[CH:30][C:29]([Cl:33])=[CH:28][C:27]=1B(O)O>>[Cl:25][C:26]1[C:31]([Cl:32])=[CH:30][C:29]([Cl:33])=[CH:28][C:27]=1[C:5]1[C:4]([C:3]([OH:24])=[O:2])=[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 51065082,3,5-Trichlorophenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679886HCID 86679886, compoundYield 2%

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 2,3,5-trichlorophenylboronic acid (available from Alfa Aesar; 113 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′,3′,5′-trichloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (2.5 mg, 2%). 1H NMR (300 MHz, DMSO-d6) δ 13.27 (br s, 1H), 8.58 (d, J=1.9 Hz, 1H), 8.50 (s, 1H), 8.34 (d, J=2.1 Hz, 1H), 8.30 (d, J=7.9 Hz, 1H), 8.10 (dd, J=8.4, 2.0 Hz, 1H), 8.00 (d, J=2.4 Hz, 1H), 7.88 (d, J=2.4 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.64 (d, J=2.4 Hz, 1H), 7.47-7.53 (m, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-ca51d93a413a4bdebc65da562437bfc9
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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