tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate → tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)piperidine-1-carboxylate

HRID 531865Notes

Reaction equation

HRID 531865 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:54]=[C:55]([F:57])[CH:56]=1)[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([C:26]5[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH:27]=5)=[C:22]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:21]=4)[CH:18]=3)[N:13]([S:44]([C:47]3[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=3)(=[O:46])=[O:45])[CH:12]=2)=[N:7]1>[N+](C1C=C(C=CC=1)CN1C=C(B2OC(C)(C)C(C)(C)O2)C=N1)([O-])=O.[OH-].[Pd+2].[OH-]>[F:57][C:55]1[CH:54]=[C:4]([CH:3]=[C:2]([F:1])[CH:56]=1)[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([CH: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]([NH:39][S:40]([CH3:43])(=[O:41])=[O:42])[CH:21]=4)[CH:18]=3)[N:13]([S:44]([C:47]3[CH:48]=[CH:49][C:50]([CH3:51])=[CH:52][CH:53]=3)(=[O:46])=[O:45])[CH:12]=2)=[N:7]1

Participants

4

Reactant 1

HCID 118523958tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)-5,6-dihydropyridine-1 (2H)-carboxylate

Product 1

HCID 118524054tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)piperidine-1-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 900309041H-Pyrazole, 1-[(3-nitrophenyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Solvent

Procedure

Using similar reaction conditions as described in step-ii of example-82, tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-(methylsulfonamido)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (250 mg, 0.307 mmol) was reduced with palladium hydroxide (250 mg) in ethyl acetate/ethanol 10/10 mL to afford 200 mg (80% yield) of the titled compound. MS: m/z=817.7 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-3324e9449f1d48d089fa407520d5010f
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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