2-Methoxypyridine-3-boronic acid hydrate → Methyl 4-(4-chloro-2-methoxyphenoxy)-2-fluoro-5-(2-methoxypyridin-3-yl)benzoate

HRID 1620331Notes

Reaction equation

Br[C:2]1[C:3]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[O:21][CH3:22])=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].O.[CH3:24][O:25][C:26]1[C:31](B(O)O)=[CH:30][CH:29]=[CH:28][N:27]=1>O>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][C:3]2[C:2]([C:31]3[C:26]([O:25][CH3:24])=[N:27][CH:28]=[CH:29][CH:30]=3)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:12])[CH:4]=2)=[C:15]([O:21][CH3:22])[CH:16]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Prepared according to Preparation 2 using methyl 5-bromo-4-(4-chloro-2-methoxyphenoxy)-2-fluorobenzoate (Preparation 17, 0.165 g, 0.423 mmol) and (2-methoxypyridin-3-yl)boronic acid mono hydrate (0.109 g, 0.637 mmol) with an extra addition of water (0.5 mL) and heating for 18 hours at 50° C. The crude product was purified by silica gel chromatography eluting with 0 to 10% EtOAc in DCM to afford the title compound as a clear gum (47.7 mg).

Workup

customPrepared
customThe crude product was purified by silica gel chromatography
washeluting with 0 to 10% EtOAc in DCM

Sources & evidence

ORD record: ord-53b7ae23ca284f8dbb0986ecdd3880b7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772343B2

Reaction notes

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