Triethylamine → (5-Bromo-3-fluoropyridin-2-yl)methyl methanesulfonate

HRID 341041Notes

Reaction equation

HRID 341041 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[CH3:18][S:19]([O:9][CH2:8][C:5]1[C:4]([F:10])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57416937(5-Bromo-3-fluoropyridin-2-yl)methanol

Product 1

HCID 86668676(5-Bromo-3-fluoropyridin-2-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(5-Bromo-3-fluoropyridin-2-yl)methanol (0.20 g, 0.99 mmol) was dissolved in dichloromethane (5 mL), cooled to 0° C. and treated with triethylamine (0.15 mL, 1.1 mmol, 1.1 equiv) and methanesulfonyl chloride (0.085 mL, 1.1 mmol, 1.1 equiv). After 15 minutes, the mixture was diluted with dichloromethane (100 mL) and washed once with sodium bicarbonate (20 mL, aqueous saturated) and brine (50 mL), dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

  1. washwashed once with sodium bicarbonate (20 mL, aqueous saturated) and brine (50 mL)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66f59257680747539b5e9c98e033cd70
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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