tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-nitrophenyl)piperazine-1-carboxylate → tert-butyl 4-(2-amino-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

HRID 531680Notes

Reaction equation

HRID 531680 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([N:26]5[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]5)=[C:22]([N+:39]([O-])=O)[CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1>[Pd].CO>[NH2:39][C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[C:19]3[C:11]([C:9]4[CH:8]=[N:7][N:6]([CH2:5][C:4]5[CH:42]=[CH:43][CH:44]=[C:2]([F:1])[CH:3]=5)[CH:10]=4)=[CH:12][NH:13][C:14]3=[N:15][CH:16]=2)[CH:25]=[CH:24][C:23]=1[N:26]1[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]1

Participants

4

Reactant 1

HCID 90031482tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 90030996tert-butyl 4-(2-amino-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateYield 105.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Using similar reaction conditions as described in example-8, tert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-nitrophenyl)piperazine-1-carboxylate (90 mg, 0.15 mmol) was reduced by 10% palladium on carbon (10 mg, 10% W/W) in methanol (10 mL) to yield crude 90 mg of the titled compound. MS: m/z=567.8 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-80d659d588cb48c18961e6f4c84b18cc
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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