2,4-Difluoroaniline → Ethyl 2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetate

HRID 524383Notes

Reaction equation

HRID 524383 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH:17]2[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:22]=1[NH2:23]>>[CH:17]1([S:14]([C:11]2[CH:12]=[CH:13][C:8]([CH:2]([NH:23][C:22]3[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:21]=3[F:20])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:9][CH:10]=2)(=[O:16])=[O:15])[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 97092,4-DifluoroanilineHCID 59610021Ethyl 2-bromo-2-(4-cyclopropylsulfonylphenyl)acetate

Product 1

HCID 68182723Ethyl 2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetate

Conditions

Temperature
150 °C

Procedure

Ethyl 2-bromo-2-(4-cyclopropylsulfonylphenyl)acetate (0.8 g, 2.30 mmol) [obtained as described in WO2009/047798 A2; Example A1] and 2,4-difluoroaniline (3.0 mL) mixed together and heated at 150° C. in a seal tube for 12 hrs. Reaction mixture was cooled to rt and purified by column chromatography using 20% ethyl acetate in hexane as eluent to provide ethyl 2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetate (0.65 g).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to rt
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-8291fbf947ae46bcbe5461e3b7c0d8c8
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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