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

HRID 531846Notes

Reaction equation

HRID 531846 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:50]=[C:51]([F:53])[CH:52]=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]([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]([F:39])[CH:21]=4)[CH:18]=3)[N:13]([S:40]([C:43]3[CH:49]=[CH:48][C:46]([CH3:47])=[CH:45][CH:44]=3)(=[O:42])=[O:41])[CH:12]=2)[CH:8]=[N:7]1>COC1C=CC(CN2C=C(B3OC(C)(C)C(C)(C)O3)C=N2)=CC=1.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:3]=[C:4]([CH:50]=[C:51]([F:53])[CH:52]=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]([CH:26]5[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33])[CH2:30][CH2:31]5)=[C:22]([F:39])[CH:21]=4)[CH:18]=3)[N:13]([S:40]([C:43]3[CH:44]=[CH:45][C:46]([CH3:47])=[CH:48][CH:49]=3)(=[O:41])=[O:42])[CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 1

HCID 118523940tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)-5,6-di hydropyridine-1(2H)-carboxylate

Product 1

HCID 118524078tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)piperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 534402131-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-82, tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)-5,6-di hydropyridine-1(2H)-carboxylate (103 mg, 0.139 mmol) was reduced with palladium hydroxide (50 mg) in ethyl acetate/ethanol 5/15 mL to afford 102 mg (99% yield) of the titled compound. MS: m/z=742.6 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-e097b24aedb84f2088cee842af6b7da0
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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