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 383851Notes

Reaction equation

HRID 383851 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-ea8f4e49f220476a97feea961d8784e0
Source dataset
uspto-grants-2013_02
Patent number
US08367676B2

Reaction notes

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