Triethylamine → 5-(3-Chloroprop-1-EN-1-YL)-2-(4-fluorophenyl)pyridine

HRID 238301Notes

Reaction equation

HRID 238301 reaction equation
CS([Cl:5])(=O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:18]=[CH:17][C:16]([CH:19]=[CH:20][CH2:21]O)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[Cl:5][CH2:21][CH:20]=[CH:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=2)=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 688219193-(6-(4-Fluorophenyl)pyridin-3-yl)prop-2-en-1-ol

Product 1

HCID 688221025-(3-Chloroprop-1-EN-1-YL)-2-(4-fluorophenyl)pyridineYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

436 mg (3.8 mmol) of methanesulfonyl chloride were slowly added at room temperature to 513 mg (2.24 mmol) of 3-(6-(4-fluorophenyl)pyridin-3-yl)prop-2-en-1-ol and 679 mg (6.71 mmol) of triethylamine in 20 ml of dichloromethane. The mixture was stirred at room temperature for 6 h and extracted with a sodium hydrogencarbonate solution. The organic phase was evaporated to yield 550 mg of the title compound. MS: M+H+=248.1.

Workup

  1. extractionextracted with a sodium hydrogencarbonate solution
  2. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-8d5d00b21e0943be82c2cad4c83c6aea
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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