Methanesulfonyl chloride → HCID 86672755, compound

HRID 2172961Notes

Reaction equation

HRID 2172961 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][S:20]([CH3:19])(=[O:22])=[O:21])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 86672755HCID 86672755, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred 0° C. solution of (2-bromo-pyridin-4-yl)-methanol (3.00 g, 16.0 mmol) and N,N-diisopropylethylamine (8.3 mL, 48 mmol) in dichloromethane (30 mL) is added methanesulfonyl chloride (1.30 mL, 16.8 mmol). The resulting mixture is warmed to room temperature. After 1 hour, the mixture is diluted with dichloromethane (20 mL) and washed with saturated aqueous ammonium chloride (3×10 mL), saturated aqueous sodium bicarbonate (10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated to afford crude methanesulfonic acid 2-bromo-pyridin-4-ylmethyl ester, which is used without purification.

Workup

  1. washwashed with saturated aqueous ammonium chloride (3×10 mL), saturated aqueous sodium bicarbonate (10 mL), brine (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9698243b62334df89aff0a93833b8a8a
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

Loading…