Triethylamine → Methanesulfonic acid 2-(6-(2-fluorophenyl)pyridin-3-yloxy)ethyl ester

HRID 1896702Notes

Reaction equation

HRID 1896702 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][OH:22])=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 691055892-(6-(2-Fluorophenyl)pyridin-3-yloxy)ethanol

Product 1

HCID 86621525Methanesulfonic acid 2-(6-(2-fluorophenyl)pyridin-3-yloxy)ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

217.1 mg (1.89 mmol) of methanesulfonyl chloride were added dropwise with cooling to 340 mg (1.46 mmol) of 2-(6-(2-fluorophenyl)pyridin-3-yloxy)ethanol and 442.5 mg (4.37 mmol) of triethylamine in 25 ml of methylene chloride. After 7 h at room temperature, the mixture was extracted with water, and the organic phase was separated and concentrated. Yield: 394 mg (87%).

Workup

  1. extractionthe mixture was extracted with water
  2. customthe organic phase was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-86246f6ed88945b699b64f9559432195
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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