Pyridine → Ethyl 3-(2-chloro-3,5-difluorophenylamino)-2-methyl-3-oxopropanoate

HRID 1431470Notes

Reaction equation

HRID 1431470 reaction equation
[CH3:1][CH:2]([C:8]([O:10]CC)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C=CC=CC=1.[Cl:19][C:20]1[C:26]([F:27])=[CH:25][C:24]([F:28])=[CH:23][C:21]=1[NH2:22]>>[Cl:19][C:20]1[C:26]([F:27])=[CH:25][C:24]([F:28])=[CH:23][C:21]=1[NH:22][C:8](=[O:10])[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 3

HCID 1049PyridineHCID 11857Diethyl methylmalonateHCID 27364942-Chloro-3,5-difluoroaniline

Product 1

HCID 59631036Ethyl 3-(2-chloro-3,5-difluorophenylamino)-2-methyl-3-oxopropanoate

Procedure

The ester was prepared according to Procedure A using diethyl 2-methylmalonate (6.31 mL, 36.7 mmol), pyridine (3.96 mL, 48.9 mmol) and 2-chloro-3,5-difluoroaniline (4.00 g, 24.46 mmol) over 3 days. The residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes) to give ethyl 3-(2-chloro-3,5-difluorophenylamino)-2-methyl-3-oxopropanoate as a red oil. Mass Spectrum (ESI) m/e=292.0 (M+1).

Workup

  1. customThe ester was prepared
  2. customThe residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-036fbf923d9142a9871086bcacd61640
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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