Water → HCID 86676390, compound

HRID 920356Notes

Reaction equation

HRID 920356 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[F:14].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>ClCCl>[CH3:26][S:27]([O:13][CH2:12][C:9]1[CH:10]=[N:11][C:6]([O:5][C:4]2[CH:15]=[CH:16][C:17]([F:18])=[C:2]([F:1])[CH:3]=2)=[C:7]([F:14])[CH:8]=1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71236848HCID 71236848, compound

Product 1

HCID 86676390HCID 86676390, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of (6-(3,4-difluorophenoxy)-5-fluoropyridin-3-yl)methanol (8.4 g, 26.7 mmol) and triethylamine (6.89 mL, 49.4 mmol) in dichloromethane (DCM) (100 mL) was added methanesulfonyl chloride (4.8 g, 41.9 mmol). The reaction mixture was stirred at 20° C. for 2 hr. then 200 mL of H2O was added. The organic layer was separated, dried over Na2SO4, and then concentrated under reduced pressure to give (6-(3,4-difluorophenoxy)-5-fluoro pyridin-3-yl)methyl methanesulfonate (8 g, 42.3%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-62e76ede16a746dd826dc10d5854e10b
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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