Pyridine → HCID 59631474, compound

HRID 1431321Notes

Reaction equation

HRID 1431321 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.[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:27])=[C:24]([CH:26]=1)[NH2:25]>>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH3:27])=[C:24]([NH:25][C:8](=[O:10])[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:26]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 11857Diethyl methylmalonateHCID 677745-Fluoro-o-toluidine

Product 1

HCID 59631474HCID 59631474, compound

Procedure

The ester was prepared according to Procedure A using diethyl 2-methylmalonate (6.18 mL, 36.0 mmol), pyridine (3.88 mL, 47.9 mmol) and 5-fluoro-2-methylaniline (3.00 g, 23.97 mmol). Heating continued for 4 days. The residue was purified by column chromatography on silica gel (0-30% EtOAc/hexanes) to give ethyl 3-(5-fluoro-2-methylphenylamino)-2-methyl-3-oxopropanoate as a tan solid. Mass Spectrum (ESI) m/e=254.2, (M+1).

Workup

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

Sources & evidence

ORD record
ord-ec0cd2d918ff48308cf2dee8a7163436
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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