Potassium Carbonate → N-(3-(2-(2-methoxyphenyl)-2-oxoethoxy)phenyl)picolinamide

HRID 38240

Reaction equation

C([O-])([O-])=O.[K+].[K+].Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])=[O:10].[OH:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH:23]=[CH:24][CH:25]=1>CC(C)=O>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:9](=[O:10])[CH2:8][O:19][C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

According to Scheme 2: K2CO3 (2.33 mmol, 323 mg) and 2-bromo-1-(2-methoxyphenyl)ethanone (0.47 mmol, 107 mg) were added sequentially to a solution of N-(3-hydroxyphenyl)picolinamide (0.47 mmol, 100 mg) in acetone (3 mL). The reaction mixture was stirred at 50° C. for 14 hours. After filtration and evaporation, the crude product was diluted with water and with DCM. The organic phase was washed with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was triturated with Et2O to obtain N-(3-(2-(2-methoxyphenyl)-2-oxoethoxy)phenyl)picolinamide (0.26 mmol, 94 mg, 55%) as a yellow solid.

Workup

filtrationAfter filtration and evaporation
additionthe crude product was diluted with water and with DCM
washThe organic phase was washed with brine
dry with materialwas dried over MgSO4
filtrationwas filtered
concentrationwas concentrated under reduced pressure
customThe crude product was triturated with Et2O

Sources & evidence

ORD record: ord-ca2c645abd7844929f0c2959f162356b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524726B2

Linked notes

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