Tin tetrachloride → 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide

HRID 456665Notes

Reaction equation

HRID 456665 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]([C:12]2[NH:13][CH:14]=[CH:15][CH:16]=2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:17][C:18]1[N:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].[Sn](Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[C:1]1([C@@H:7]([NH:9][C:10]([C:12]2[NH:13][C:14]([C:20]([C:19]3[C:18]([Cl:17])=[N:26][CH:25]=[CH:24][CH:23]=3)=[O:21])=[CH:15][CH:16]=2)=[O:11])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 27745412-Chloronicotinoyl chlorideHCID 86592245HCID 86592245, compound

Product 1

HCID 865922465-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amideYield 35%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide (800 mg, 3.7 mmol) and 2-chloronicotinoyl chloride (95 mg, 5.4 mmol) in dry benzene (10 mL) at 0° C. was added dropwise a solution of tin (IV) chloride (1.75 g) in benzene (5 mL). The mixture was allowed to warm up slowly to room temperature and stirred for overnight. The reaction was concentrated, diluted with ethyl acetate, washed with water, 1N NaOH, brine, dried and concentrated. The residue was purified on a silica gel column to give 458 mg (35%) of 5-(2-chloro-pyridine-3-carbonyl)-1H-pyrrole-2-carboxylic acid ((S)-1-phenyl-ethyl)-amide.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water, 1N NaOH, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-6f88d3a0c41645bfaaf8233d8d2439c6
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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