1-(5-(2-Bromoethyl)indolin-1-yl)ethanone → 7-(4-(2-(1-Acetylindolin-5-yl)ethyl)piperazin-1-yl)-5-fluoro-N,N-dimethylbenzofuran-2-carboxamide

HRID 535679Notes

Reaction equation

HRID 535679 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:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34](=[O:36])[CH3:35])[CH2:29][CH2:28]2>>[C:34]([N:30]1[C:31]2[C:27](=[CH:26][C:25]([CH2:24][CH2:23][N:19]3[CH2:20][CH2:21][N:16]([C:4]4[C:5]5[O:9][C:8]([C:10]([N:12]([CH3:14])[CH3:13])=[O:11])=[CH:7][C:6]=5[CH:15]=[C:2]([F:1])[CH:3]=4)[CH2:17][CH2:18]3)=[CH:33][CH:32]=2)[CH2:28][CH2:29]1)(=[O:36])[CH3:35]

Participants

3

Reactant 2

HCID 517132361-(5-(2-Bromoethyl)indolin-1-yl)ethanoneHCID 596367255-fluoro-N,N-dimethyl-7-(piperazin-1-yl)benzofuran-2-carboxamide

Product 1

HCID 596367787-(4-(2-(1-Acetylindolin-5-yl)ethyl)piperazin-1-yl)-5-fluoro-N,N-dimethylbenzofuran-2-carboxamide

Procedure

The compound was prepared according to the procedure disclosed in Example 50 starting from 5-fluoro-N,N-dimethyl-7-(piperazin-1-yl)benzofuran-2-carboxamide (0.10 g, 0.35 mmol) (Example 50g) and 1-(5-(2-bromoethyl)indolin-1-yl)ethanone (0.13 g, 0.49 mmol) (Example 49b). The product was purified by preparative HPLC to give the title compound.

Workup

  1. customThe compound was prepared
  2. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-7184396a6c474d239b1057468b9d26c8
Source dataset
uspto-grants-2014_10
Patent number
US08859534B2

Reaction notes

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