Methanesulfonyl chloride → Methanesulfonic acid 1-(6-fluoro-4-iodo-pyridin-3-yl)-ethyl ester

HRID 1640881Notes

Reaction equation

HRID 1640881 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]1[N:12]=[CH:11][C:10]([CH:13]([OH:15])[CH3:14])=[C:9]([I:16])[CH:8]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>[F:6][C:7]1[N:12]=[CH:11][C:10]([CH:13]([O:15][S:2]([CH3:1])(=[O:4])=[O:3])[CH3:14])=[C:9]([I:16])[CH:8]=1

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 667380961-(6-Fluoro-4-iodo-pyridin-3-yl)-ethanol

Product 1

HCID 86641872Methanesulfonic acid 1-(6-fluoro-4-iodo-pyridin-3-yl)-ethyl esterYield 64.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Add methanesulfonyl chloride (1.93 g, 16.8 mmol) to a solution of 1-(6-fluoro-4-iodo-pyridin-3-yl)-ethanol (1.5 g, 5.6 mmol) and diisopropylethylamine (2.2 g, 16.8 mmol) in DCM (50 mL) at 0° C. Continue to stir the mixture at 0° C. to RT for 4 h. Dilute the reaction mixture with diluted sodium carbonate. Extract the product into chloroform. Dry the organic phase over sodium sulfate. Concentrate the solution in vacuo. Purify the crude by column chromatography (20% ethyl acetate in hexane) to afford the title compound as a white solid (1.24 g, 64%). MS (ES) m/z 346 [M+1]+.

Workup

  1. extractionExtract the product into chloroform
  2. dry with materialDry the organic phase over sodium sulfate
  3. concentrationConcentrate the solution in vacuo
  4. customPurify the crude by column chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d9a872129cee474496a09887437bd7e9
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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