Pyridine → Ethyl{[(2-fluorophenyl)acetyl]amino}(pyridin-2-yl)acetate

HRID 1875439Notes

Reaction equation

[NH2:1][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].ClCCl.N1C=CC=CC=1.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31](Cl)=[O:32]>C(OCC)(=O)C>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([NH:1][C:31](=[O:32])[CH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[F:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

2.50 g (12.1 mmol) of ethyl amino(pyridin-2-yl)acetate [G. van Zyl et al., J. Org. Chem. 1961, 26, 3373] are introduced into 20 ml of dichloromethane and, after addition of 4.9 ml (60.3 mmol) of pyridine, cooled to 0° C. A solution of 1.86 g (12.1 mmol) of (2-fluorophenyl)acetyl chloride is then slowly added, and the mixture is stirred at 0° C. for 30 min and then at RT for 2 h. It is diluted with ethyl acetate, washed with sodium bicarbonate solution and dried over sodium sulfate. The crude product is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1). 2.9 g (76% of theory) of the desired product are obtained.

Workup

waitat RT for 2 h
washwashed with sodium bicarbonate solution
dry with materialdried over sodium sulfate
customThe crude product is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-44e0f0e40f9942dda44ef6d4750baa38
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309551B2

Reaction notes

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