Triethylamine → (5-Fluoropyridin-2-yl)methyl methanesulfonate

HRID 2041196Notes

Reaction equation

HRID 2041196 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][OH:14])=[N:11][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[F:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][O:14][S:2]([CH3:1])(=[O:4])=[O:3])=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 24729312(5-Fluoropyridin-2-yl)methanol

Product 1

HCID 57656057(5-Fluoropyridin-2-yl)methyl methanesulfonateYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonyl chloride (1.8 mL, 23.5 mmol) to a solution of (5-fluoro-pyridin-2-yl)-methanol (2.5 g, 19.7 mmol) and triethylamine (8.2 mL, 59.0 mmol) in DCM (150 mL) at 0° C. under nitrogen. Stir the mixture for 30 min and concentrate in vacuo. Dilute with water (20 mL) and extract the mixture with EtOAc (3×50 mL). Combine the organic extracts and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc to obtain the desired intermediate (2.2 g, 54%).

Workup

  1. concentrationconcentrate in vacuo
  2. additionDilute with water (20 mL)
  3. extractionextract the mixture with EtOAc (3×50 mL)
  4. concentrationCombine the organic extracts and concentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc

Sources & evidence

ORD record
ord-1fae5b0a6b4a4b87a356c552b5f1c85d
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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