tert-butyl 4-(1H-indazol-5-yl)-3,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylate

HRID 1520016Notes

Reaction equation

HRID 1520016 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH:15]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1>CO.[Pd]>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]3[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 67981587tert-butyl 4-(1H-indazol-5-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 49760224tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(1H-indazol-5-yl)-3,6-dihydropyridine-1(2H)-carboxylate (200 mg; 0.67 mmol; 1.0 eq.) in MeOH (6 mL) was hydrogenated (10 bars) in a Paar instrument in presence of Pd/C (10% Pd moistened 50% H2O; 7.11 mg; 0.07 mmol; 0.10 eq.) at RT. After 12 h, the reaction mixture was filtered through a celite pad and the filtrate was concentrated to dryness to give the title compound as a grey foam (200 mg; 99%). 1H NMR (300 MHz, DMSO-d6) δ 12.94 (brs, 1H), 7.98 (s, 1H), 7.56 (s, 1H), 7.49-7.43 (m, 1H), 7.28-7.22 (m, 1H), 4.18-4.02 (m, 2H), 2.99-2.67 (m, 3H), 1.83-1.73 (m, 2H), 1.65-1.46 (m, 2H), 1.42 (s, 9H).

Workup

  1. customat RT
  2. filtrationthe reaction mixture was filtered through a celite pad
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-2af274c7dc6447e186cac314bf225f76
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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