2,3-Dichlorobenzeneboronic acid → HCID 86679889, compound

HRID 1519399Notes

Reaction equation

HRID 1519399 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][CH:29]=[CH:28][C:27]=1B(O)O>>[Cl:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[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 27346612,3-Dichlorobenzeneboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679889HCID 86679889, compoundYield 19.2%

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-dichlorophenylboronic acid (available from Combi-Blocks Inc.; 76 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′,3′-dichloro-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (19 mg, 19%). 1H NMR (400 MHz, DMSO-d6) δ 13.13 (br s, 1H), 8.56 (d, J=1.8 Hz, 1H), 8.49 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.29 (dd, J=7.9, 1.9 Hz, 1H), 8.09 (dd, J=8.3, 2.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.66 (dd, J=8.0, 1.5 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 7.43 (t, J=7.8 Hz, 1H), 7.33 (dd, J=7.7, 1.4 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-a3693669fa2c4f4a83554070a65b7eed
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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