Ethyl bromopyruvate → N-[2-(Ethyloxycarbonyl)imidazo[1,2-a]pyrid-6-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 1944015Notes

Reaction equation

HRID 1944015 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([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:4][CH:3]=1.Br[CH2:30][C:31](=O)[C:32]([O:34][CH2:35][CH3:36])=[O:33]>C(#N)C>[CH2:35]([O:34][C:32]([C:31]1[N:1]=[C:2]2[CH:3]=[CH:4][C:5]([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:6][N:7]2[CH:30]=1)=[O:33])[CH3:36]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 66863527N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

Product 1

HCID 66864042N-[2-(Ethyloxycarbonyl)imidazo[1,2-a]pyrid-6-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamideYield 40.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 22 was prepared according to a process similar to that described in step 4.3, by reacting 0.1 g (0.26 mmol) of N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)-methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 4.2, with 0.105 g (0.53 mmol) of ethyl 3-bromo-2-oxopropionate in 4 mL of acetonitrile. 0.05 g of the expected product is obtained in the form of a white solid.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-398e1f29b4504e9bb611c21e11ccc169
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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