Triethylamine → HCID 86668030, compound

HRID 538320Notes

Reaction equation

HRID 538320 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](O)([CH3:10])[CH3:9])[C:5]([F:12])=[CH:4][CH:3]=1.CS(OS(C)(=O)=O)(=O)=O.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[C:5]([F:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 86668029HCID 86668029, compound

Product 1

HCID 86668030HCID 86668030, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(6-bromo-3-fluoro-pyridin-2-yl)-propan-2-ol (22.3 g, 95 mmol) and methanesulfonic acid anhydride (49.8 g, 286 mmol) in dichloromethane was added dropwise triethylamine (53.1 ml, 381 mmol) at 0° C. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was quenched with aq. sodium carbonate solution and diluted with dichloromethane. The aqueous phase was extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo (volatile). The crude brown oil was chromatographed over silica (cyclohexane:ethyl acetate 9:1) to give the title compound as a clear liquid. 17.35 g (84% yield). TLC (cyclohexane/ethyl acetate 9:1) Rf=0.58; 1H-NMR (360 MHz, CDCl3): 7.26-7.15 (m, 2H), 5.72 (s, 1H), 5.47 (s, 1H), 2.12 (s, 3H, CH3).

Workup

  1. customThe reaction mixture was quenched with aq. sodium carbonate solution
  2. additiondiluted with dichloromethane
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo (volatile)
  8. customThe crude brown oil was chromatographed over silica (cyclohexane:ethyl acetate 9:1)

Sources & evidence

ORD record
ord-04d0671871914104a81289978b7d92ee
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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