Methanesulfonyl chloride → Methanesulfonic acid 3-fluoro-pyridin-4-ylmethyl ester

HRID 426264Notes

Reaction equation

HRID 426264 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][O:9][S:11]([CH3:10])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 49760376(3-Fluoropyridin-4-yl)methanol

Product 1

HCID 59184682Methanesulfonic acid 3-fluoro-pyridin-4-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C. TEA (44 μl, 0.314 mmol, 2 eq.) was added to (3-fluoro-pyridin-4-yl)-methanol (20 mg, 0.157 mmol, 1 eq.) in 1 mL DCM, followed by MsCl (15 μl, 0.188 mmol, 1.2 eq.) The reaction was stirred at 0° C. for 30 minutes. HPLC and LC-MS showed reaction complete. The reaction crude was concentrated down. Ethyl acetate was added and washed with saturated NAHCO3 aqueous solution. The Ethyl acetate layer was concentrated after dried over Na2SO4 to give color oil which was used directly in next step. LC-MS shows 206.1 (M+1).

Workup

  1. customAt 0° C
  2. customreaction complete
  3. customThe reaction crude
  4. concentrationwas concentrated down
  5. additionEthyl acetate was added
  6. washwashed with saturated NAHCO3 aqueous solution
  7. concentrationThe Ethyl acetate layer was concentrated
  8. dry with materialafter dried over Na2SO4
  9. customto give color oil which

Sources & evidence

ORD record
ord-a2a76b2d4c90488491a4697cea22b872
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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