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

HRID 531455Notes

Reaction equation

HRID 531455 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[C:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]=1>C(OCC)(=O)C.CO.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1

Participants

4

Reactant 1

HCID 90034216tert-butyl 4-(2-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 90030541tert-butyl 4-(2-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylateYield 99.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of tert-butyl 4-(2-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (320 mg, 0.814 mmol) in ethyl acetate/methanol 20/20 mL was added palladium hydroxide (160 mg) and stirred under hydrogen atmosphere for 7 days. The catalyst was filtered through celite and the solvent was distilled off to get 320 mg (99.37% yield) of the titled compound. MS: m/z=396.3 (M+1).

Workup

  1. filtrationThe catalyst was filtered through celite
  2. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8d8e931c74e94a7ab16371aebe9300fa
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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