Hydrogen Bromide → 5-Fluoro-N,N-dimethyl-7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxamide

HRID 383845Notes

Reaction equation

HRID 383845 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:5]2[O:9][C:8]([C:10]([N:12]([CH3:14])[CH3:13])=[O:11])=[CH:7][C:6]=2[CH:15]=1.Br[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.Br.C(N(CC)CC)C>>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH2:18][CH2:17]2)[C:5]2[O:9][C:8]([C:10]([N:12]([CH3:14])[CH3:13])=[O:11])=[CH:7][C:6]=2[CH:15]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 129138582-(2-Bromoethyl)pyridineHCID 596367255-fluoro-N,N-dimethyl-7-(piperazin-1-yl)benzofuran-2-carboxamide

Product 1

HCID 596367345-Fluoro-N,N-dimethyl-7-(4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)benzofuran-2-carboxamide

Procedure

A reaction mixture of 5-fluoro-N,N-dimethyl-7-(piperazin-1-yl)benzofuran-2-carboxamide (0.10 g, 0.35 mmol), 2-(2-bromoethyl)pyridine:HBr (0.132 g, 0.49 mmol) and triethylamine (0.12 mL, 0.88 mmol) was heated at 80° C. over night. The product was purified by preparative HPLC to give the title compound. Yield: 0.091 g (65%).

Workup

  1. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-b7dec469b6f1415496db1ae6d27eff3e
Source dataset
uspto-grants-2013_02
Patent number
US08367676B2

Reaction notes

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