2-Bromo-1-(thiophen-2-yl)ethan-1-one → N-[2-(Thien-2-yl)imidazo[1,2-a]pyrid-7-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 1944002Notes

Reaction equation

HRID 1944002 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([F:20])=[CH:15][CH:14]=3)=[O:10])[CH:5]=[CH:4][N:3]=1.Br[CH2:30][C:31]([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)=O>C(#N)C>[S:34]1[CH:35]=[CH:36][CH:37]=[C:33]1[C:31]1[N:1]=[C:2]2[CH:7]=[C:6]([NH:8][C:9]([C:11]3[N:12]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([F:20])=[CH:15][CH:14]=4)=[O:10])[CH:5]=[CH:4][N:3]2[CH:30]=1

Participants

4

Reactant 2

HCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-oneHCID 66863747N-[2-aminopyrid-4-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

Product 1

HCID 66863419N-[2-(Thien-2-yl)imidazo[1,2-a]pyrid-7-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamideYield 20.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 11 was prepared according to a process similar to that described in step 10.2, by reacting 0.1 g (0.26 mmol) of N-[2-aminopyrid-4-yl]-5-fluoro-1-[(3-fluoro-phenyl)methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 10.1, with 0.11 g (0.53 mmol) of 2-bromo-1-(thien-2-yl)ethanone in 4 mL of acetonitrile. 0.026 g of the expected product is thus obtained in the form of a beige-coloured solid.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-a7883e9ca9f64ef383b26bfc616bde00
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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