Tin tetrachloride → 5-(2,6-difluro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide

HRID 456674Notes

Reaction equation

HRID 456674 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[NH:12][C:13](C3C4C(=CC=C(C(F)(F)F)C=4)NN=3)=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[F:29][C:30]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:31]=1[C:32](Cl)=[O:33].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[NH:12][C:13]([C:32](=[O:33])[C:31]3[C:30]([F:29])=[CH:38][CH:37]=[CH:36][C:35]=3[F:39])=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24287Tin tetrachlorideHCID 874382,6-Difluorobenzoyl chlorideHCID 1355312255-(5-Trifluoromethyl-1H-indazol-3-yl)-1H-pyrrole-2-carboxylic Acid (3-fluoro-phenyl)-amide

Product 1

HCID 859345855-(2,6-difluro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amideYield 12.2%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide (1 g, 4.9 mmol) (Example 55) and 2,6-difluro-benzoyl chloride 1.5 g, 8.8 mmol) (Aldrich, Milwaukee, Wis.) in benzene (10 mL) at room temperature was added a solution of tin (IV) chloride (1 mL, 2.26 g, 8.6 mmol). After stirring at room temperature for overnight, the reaction was diluted with water and ethyl acetate. The organic layer was washed with 2N NaOH, dried and purified on a silica gel column to give 205 mg of 5-(2,6-difluro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide as a white solid.

Workup

  1. washThe organic layer was washed with 2N NaOH
  2. customdried
  3. custompurified on a silica gel column

Sources & evidence

ORD record
ord-4ee6331a38964e75a64f2115f95d7213
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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