Triethylamine → (5-Bromo-2-chloropyridin-4-yl)methyl methanesulfonate

HRID 531242Notes

Reaction equation

HRID 531242 reaction equation
[Br:1][C:2]1[C:3]([CH2:9][OH:10])=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:18][S:19]([O:10][CH2:9][C:3]1[C:2]([Br:1])=[CH:7][N:6]=[C:5]([Cl:8])[CH:4]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53401482(5-Bromo-2-chloropyridin-4-yl)methanol

Product 1

HCID 90009114(5-Bromo-2-chloropyridin-4-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 0° C. solution of (5-bromo-2-chloropyridin-4-yl)methanol (1.96 g, 8.81 mmol) in CH2Cl2 (25 mL) was treated with triethylamine (2.456 ml, 17.62 mmol) and methanesulfonyl chloride (0.824 ml, 10.57 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was diluted with additional CH2Cl2, then washed with aqueous NaHCO3, followed by brine. The organic was dried over sodium sulfate, filtered and the filtrate evaporated. The crude was purified by silica gel chromatography to give the titled compound. 1H NMR (CDCl3, 500 MHz): δ 8.50 (s, 1H), 7.47 (s, 1H), 5.24 (s, 2H), 3.16 (s, 3H).

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialThe organic was dried over sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customThe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0315a97b04b940fa9ef4e26d2d3a406a
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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