5-Chloropyridine-3-boronic acid → HCID 86679851, compound

HRID 1519355Notes

Reaction equation

HRID 1519355 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:27]=[C:28](B(O)O)[CH:29]=[N:30][CH:31]=1>>[Cl:25][C:26]1[CH:27]=[C:28]([C:5]2[CH:6]=[CH:7][C:8]([C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=4)[N:14]=3)=[CH:9][C:4]=2[C:3]([OH:2])=[O:24])[CH:29]=[N:30][CH:31]=1

Participants

3

Reactant 2

HCID 201118775-Chloropyridine-3-boronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679851HCID 86679851, compoundYield 8.7%

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 5-chloropyridine-3-boronic acid (available from Combi-Blocks Inc.; 63 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2-(5-chloro-pyridin-3-yl)-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid (8 mg, 8%). 1H NMR (400 MHz, DMSO-d6) δ 13.38 (br s, 1H), 8.66 (d, J=2.3 Hz, 1H), 8.47-8.55 (m, 3H), 8.34 (d, J=2.0 Hz, 1H), 8.29 (dd, J=8.0, 1.8 Hz, 1H), 8.10 (dd, J=8.5, 2.0 Hz, 1H), 8.02 (t, J=2.0 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.64 (d, J=7.8 Hz, 1H).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-c9d18b7dbf41427f9a9727e978db3128
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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