Ethyl bromopyruvate → N-[2-(Ethyloxycarbonyl)imidazo[1,2-a]pyrid-7-yl]-5-trifluoromethyl-1-[(3-fluoro-phenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1944011Notes

Reaction equation

HRID 1944011 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:14]3=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=[C:13]3[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.Br[CH2:33][C:34](=O)[C:35]([O:37][CH2:38][CH3:39])=[O:36]>C(#N)C>[CH2:38]([O:37][C:35]([C:34]1[N:1]=[C:2]2[CH:7]=[C:6]([NH:8][C:9]([C:11]3[N:23]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=4)[C:14]4=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:18]=[C:13]4[CH:12]=3)=[O:10])[CH:5]=[CH:4][N:3]2[CH:33]=1)=[O:36])[CH3:39]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 66863300N-[2-aminopyrid-4-yl]-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

Product 1

HCID 66863391N-[2-(Ethyloxycarbonyl)imidazo[1,2-a]pyrid-7-yl]-5-trifluoromethyl-1-[(3-fluoro-phenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 53.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound is prepared according to a process similar to that described in step 15.3, by reacting 0.197 g (0.46 mmol) of N-[2-aminopyrid-4-yl]-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide, prepared according to the protocol described in step 15.2, with 0.179 g (0.92 mmol) of ethyl 3-bromo-2-oxopropionate in 5 mL of acetonitrile. 130 mg of the expected product are obtained.

Workup

  1. customThe compound is prepared
  2. customprepared

Sources & evidence

ORD record
ord-d2c300407ad7438e946d293e491c2c2e
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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