Water → HCID 57792065, compound

HRID 889623Notes

Reaction equation

HRID 889623 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH:19][C:20]([C:22]1[S:23][CH:24]=[C:25]([NH2:27])[CH:26]=1)=[O:21].[Br:28]N1C(=O)CCC1=O.O>O1CCCC1>[CH3:18][C:4]1[CH:5]=[C:6]([C:8]([F:17])([C:13]([F:14])([F:15])[F:16])[C:9]([F:11])([F:12])[F:10])[CH:7]=[C:2]([CH3:1])[C:3]=1[NH:19][C:20]([C:22]1[S:23][C:24]([Br:28])=[C:25]([NH2:27])[CH:26]=1)=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 57792047HCID 57792047, compound

Product 1

HCID 57792065HCID 57792065, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-thiophene-2-carboxylic acid [2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-amide (360 mg, 0.87 mmol) (Example I3) in tetrahydrofuran (20 ml) was added N-bromosuccinimide (NBS) (155 mg, 0.87 mmol). The mixture was stirred at room temperature for 1.5 hours. Water (50 ml) was added and the organic phase was extracted twice with ethyl acetate (50 ml). The combined organic extracts were dried over sodium sulfate and the solvent evaporated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane) to give 5-bromo-4-amino-thiophene-2-carboxylic acid [2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-amide (343 mg; 80% yield); 1H-NMR (CDCl3, 400 MHz): 7.26 (s, 2H), 7.10 (s, 1H), 3.8 (s, 2H), 2.24 (s, 6H) ppm.

Workup

  1. extractionthe organic phase was extracted twice with ethyl acetate (50 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. customthe solvent evaporated
  4. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cd238f135ff14385a62e42a6f73d68d7
Source dataset
uspto-grants-2012_08
Patent number
US08252936B2

Reaction notes

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