Allyl bromide → 3-Bromo-3-(N-allyl-N-trifluoroacetyl)amino-6-methoxypyridine

HRID 2382143Notes

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]([O:15][CH3:16])[N:3]=1.[CH2:17](Br)[CH:18]=[CH2:19].C(=O)([O-])[O-].[Na+].[Na+]>CC#N>[CH2:19]([N:8]([C:7]1[C:2]([Br:1])=[N:3][C:4]([O:15][CH3:16])=[CH:5][CH:6]=1)[C:9](=[O:14])[C:10]([F:13])([F:11])[F:12])[CH:18]=[CH2:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-(2-bromo-6-methoxy-pyridin-3-yl)-2,2,2-trifluoro-acetamide (5.52 g, 18.5 mmol), allyl bromide (3.57 g, 27.7 mmol) and sodium carbonate (5.1 g, 11 mmol) in CH3CN (60 mL) is stirred at 80° C. for 3 h. The mixture is filtered and the filtrate is concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with 0-60% DCM in heptane to afford N-allyl-N-(2-bromo-6-methoxy-pyridin-3-yl)-2,2,2-trifluoro-acetamide (5.55 g) as an oil. 1H NMR (300 MHz, CDCl3): δ 3.66 (q, H), 4.00 (s, H), 5.95 (q, H), 5.08-5.30 (q, 2H), 5.75-5.94 (m, H), 6.74 (d, H), 7.38 (d, H).

Workup

filtrationThe mixture is filtered
concentrationthe filtrate is concentrated in vacuo
customThe residue is purified by silica gel column chromatography
washeluting with 0-60% DCM in heptane

Sources & evidence

ORD record: ord-2186864895ef47638eba4c76f348be66
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258130B2

Reaction notes

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