Benzyl Bromide → 1-Benzyl-2-((tert-butoxycarbonylamino)methyl)-5-fluoropyridinium bromide

HRID 60775Notes

Reaction equation

[CH2:1]([Br:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:14][CH:15]=1>CC(C)=O>[Br-:8].[CH2:1]([N+:14]1[CH:15]=[C:10]([F:9])[CH:11]=[CH:12][C:13]=1[CH2:16][NH:17][C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of benzyl bromide (4.21 mmol, 0.5 mL), tert-butyl (5-fluoropyridin-2-yl)methylcarbamate (3.49 mmol, 0.79 g) and acetone (4 mL) in a sealed tube was heated to 80° C. overnight. According to analytical HPLC, around 50% of the starting material remained. Additional benzyl bromide (33.68 mmol, 4.0 mL) was added and the reaction was continued for extra 8 h. The reaction mixture was concentrated in vacuo and loaded on a pad of silica which was rinsed with ether until benzyl bromide was gone. Then, the silica pad was rinsed with MeOH. Removal of MeOH in vacuo afforded desired product 1-benzyl-2-((tert-butoxycarbonylamino)methyl)-5-fluoropyridinium bromide as light orange solid in 43% yield. MS (ESI) 317 (M+H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
washwas rinsed with ether until benzyl bromide
washThen, the silica pad was rinsed with MeOH
customRemoval of MeOH in vacuo

Sources & evidence

ORD record: ord-242f17175c5f482ab16a6bcd6670cbcb
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440982B2

Reaction notes

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