Tin tetrachloride → 5-(2-chloro-4-nitro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide

HRID 456675Notes

Reaction equation

HRID 456675 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.[Cl:29][C:30]1[CH:38]=[C:37]([N+:39]([O-:41])=[O:40])[CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[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[CH:35]=[CH:36][C:37]([N+:39]([O-:41])=[O:40])=[CH:38][C:30]=3[Cl:29])=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 1355312255-(5-Trifluoromethyl-1H-indazol-3-yl)-1H-pyrrole-2-carboxylic Acid (3-fluoro-phenyl)-amide

Product 1

HCID 865922515-(2-chloro-4-nitro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amideYield 7.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide (1 g, 4.9 mmol) (Example 55) and 2-chloro-4-nitro-benzoyl chloride (1.5 g, 6.8 mmol) (Aldrich, Milwaukee, Wis.) in benzene (10 mL) at room temperature, was added a solution of tin (IV) chloride (1.4 mL). After stirring at room temperature for 5 hours and the usual work-up, the residue was purified on a silica gel column to give 135 mg of 5-(2-chloro-4-nitro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide as a white solid.

Workup

  1. customthe usual work-up, the residue was purified on a silica gel column

Sources & evidence

ORD record
ord-8ddb5e65bf3e46d3afbfb43edb8d6b3e
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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