Aluminium lithium hydride → N-[2-(Hydroxymethyl)imidazo[1,2-a]pyrid-7-yl]-5-trifluoromethyl-1-[(3-fluoro-phenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[CH:13]=[C:12]([NH:14][C:15]([C:17]3[N:29]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=4)[C:20]4=[N:21][CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=[C:19]4[CH:18]=3)=[O:16])[CH:11]=[CH:10][N:9]2[CH:38]=1)=[O:5])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[CH:13]=[C:12]([NH:14][C:15]([C:17]3[N:29]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=4)[C:20]4=[N:21][CH:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:24]=[C:19]4[CH:18]=3)=[O:16])[CH:11]=[CH:10][N:9]2[CH:38]=1)=[O:5])[CH3:2].[OH:3][CH2:4][C:6]1[N:7]=[C:8]2[CH:13]=[C:12]([NH:14][C:15]([C:17]3[N:29]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=4)[C:20]4=[N:21][CH:22]=[C:23]([C:25]([F:26])([F:28])[F:27])[CH:24]=[C:19]4[CH:18]=3)=[O:16])[CH:11]=[CH:10][N:9]2[CH:38]=1Participants
5
Reactant 2
Product 2
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-carboxamide
HCID 66863469N-[2-(Hydroxymethyl)imidazo[1,2-a]pyrid-7-yl]-5-trifluoromethyl-1-[(3-fluoro-phenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 36.4%Reagents, catalysts & solvents 1
Procedure
Compound 18 was prepared according to a process similar to that described in step 17.4, by reacting 0.13 g (0.25 mmol) of N-[2-(ethyloxycarbonyl)imidazo[1,2-a]pyrid-7-yl]-5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide, prepared according to the protocol described in step 18.1, with 0.32 mL of a molar solution of LiAlH4 in 4 mL of tetrahydrofuran. 22 mg of the expected product are obtained.
Workup
- customprepared
Sources & evidence
- ORD record
- ord-219e5868d12f40ba95184c5e8727ab63
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394820B2
Reaction notes
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