Allyl bromide → N-allyl-N-(2-bromo-6-fluoro-pyridin-3-yl)-2,2,2-trifluoro-acetamide

HRID 2382136Notes

Reaction equation

HRID 2382136 reaction equation
[Br:1][C:2]1[C:7]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=[C:4]([F:15])[N:3]=1.[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[Na+].[Na+]>CC#N>[CH2:18]([N:8]([C:7]1[C:2]([Br:1])=[N:3][C:4]([F:15])=[CH:5][CH:6]=1)[C:9](=[O:14])[C:10]([F:12])([F:13])[F:11])[CH:17]=[CH2:16]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 86639384N-(2-bromo-6-fluoropyridin-3-yl)-2,2,2-trifluoro-acetamide

Product 1

HCID 86639385N-allyl-N-(2-bromo-6-fluoro-pyridin-3-yl)-2,2,2-trifluoro-acetamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(2-bromo-6-fluoropyridin-3-yl)-2,2,2-trifluoro-acetamide (9.16 g, 31.9 mmol), allyl bromide (6.18 g, 47.9 mmol) and sodium carbonate (8.82 g, 63.8 mmol) in CH3CN (80 mL) is stirred at 80° C. for 2 h. The reaction mixture is concentrated in vacuo and the residue is purified by silica gel chromatography eluting with 0-60% DCM in heptane to afford N-allyl-N-(2-bromo-6-fluoro-pyridin-3-yl)-2,2,2-trifluoro-acetamide (9.05 g) as an oil. 1H NMR (300 MHz, CDCl3) δ 3.68 (q, H), 5.01 (q, H), 5.17 (d, H), 5.29 (d, H), 6.85(m, H), 7.00 (dd, H), 7.64(t, H).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residue is purified by silica gel chromatography
  3. washeluting with 0-60% DCM in heptane

Sources & evidence

ORD record
ord-dfa5e42496874f0796af78670c83492e
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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