Triethylamine → HCID 57885697, compound

HRID 1819406Notes

Reaction equation

HRID 1819406 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.CCN(CC)CC.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][S:18]([CH3:17])(=[O:20])=[O:19])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 57885697HCID 57885697, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (5-bromo-pyridin-3-yl)-methanol (2.75 g, 14.6 mmol) and Et3N (3.10 mL, 22.2 mmol) in DCM (75 mL) at −20° C. under N2 was added methanesulfonyl chloride (1.70 mL, 22.2 mmol) dropwise. After 45 min the reaction was allowed to warm to room temperature and diluted with DCM (75 mL). The reaction mixture was washed with water (75 mL), sat. NaHCO3 (2×75 mL) and brine before drying over Na2SO4. Concentration in vacuo afforded crude methanesulfonic acid 5-bromo-pyridin-3-ylmethyl ester (4.21 g) as an oil. The crude material was used in the next step without purification.

Workup

  1. washThe reaction mixture was washed with water (75 mL), sat. NaHCO3 (2×75 mL) and brine
  2. dry with materialbefore drying over Na2SO4
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-e920f46ed1b8478a85bc68a03ed95879
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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