Tin tetrachloride → 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid methylamide

HRID 456659Notes

Reaction equation

HRID 456659 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Cl:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]([C:13]([C:12]2[C:11]([Cl:10])=[N:19][CH:18]=[CH:17][CH:16]=2)=[O:14])=[CH:8][CH:9]=1)=[O:4]

Participants

6

Reactant 3

HCID 24287Tin tetrachlorideHCID 27745412-Chloronicotinoyl chlorideHCID 23273389N-Methyl-1H-pyrrole-2-carboxamide

Product 1

HCID 859347595-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid methylamideYield 35.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1H-pyrrole-2-carboxylic acid methylamide (430 mg, 3.5 mmol) and 2-chloronicotinoyl chloride (0.6 g, 3.4 mmol) in benzene (15 mL) at 0° C. was added a dropwise solution of tin (IV) chloride (1.6 g) in benzene (5 mL). The mixture was allowed to warm up slowly to room temperature and stirred for 4 hours. The reaction was diluted with ethyl acetate, washed with water, brine, dried and concentrated to give 320 mg (35%) of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid methylamide.

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ed74f60d7989442eb942fb38c901ea78
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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