Triethylamine → HCID 86668032, compound

HRID 474061Notes

Reaction equation

HRID 474061 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:12])([CH3:11])[CH2:9][OH:10])[C:5]([F:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:12])([CH3:11])[CH2:9][O:10][S:22]([CH3:21])(=[O:24])=[O:23])[C:5]([F:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86668031HCID 86668031, compound

Product 1

HCID 86668032HCID 86668032, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(6-bromo-3-fluoro-pyridin-2-yl)-propane-1,2-diol (18.29 g, 73.1 mmol) in dichloromethane (350 ml) was added triethylamine (20.39 ml, 146 mmol). Methanesulfonyl chloride (6.27 ml, 80 mmol) was added dropwise at 0° C. over 10 minutes. Stirring was continued at 0° C. for 30 minutes. The reaction mixture was washed with sat. sodium bicarbonate solution, water and brine. The organic layer was dried over sodium sulfate, filtered and evaporated. 31.46 g (crude, used without further purification in the next step). LCMS RtH5=0.81 min. (ES+ 328, 330); 1H-NMR (360 MHz, CDCl3): 7.52 (dd, 1H), 7.41 (dd, 1H), 5.13 (s, 1H, OH), 4.61 (d, 1H), 4.45 (d, 1H), 3.05 (s, 3H, CH3SO2), 1.61 (s, 3H, CH3).

Workup

  1. washThe reaction mixture was washed with sat. sodium bicarbonate solution, water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. custom31.46 g (crude, used without further purification in the next step)
  6. custom=0.81 min. (ES+ 328, 330)

Sources & evidence

ORD record
ord-56a8dbaa1b63472ba2df92692f05d6ce
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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