Ethyl 7-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate → Ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate

HRID 1497887Notes

Reaction equation

HRID 1497887 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][N:17]3[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:22]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][N:17]3[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:22]=[C:16]3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 71280489Ethyl 7-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 71281180Ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

H2(balloon) was introduced to a stirred mixture of Pd(OH)2/C (0.055 g) and ethyl 7-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate (89) (0.55 g, 1.48 mmol) in MeOH (5 mL). After 6 hours, the mixture was filtered through a pad of Celite and the solvent was evaporated to give the crude product. The residue was purified over silica using EtOAc and hexanes to give ethyl 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)imidazo[1,2-a]pyridine-3-carboxylate (90). 1H NMR (400 MHz, CD2Cl2) δ 9.27 (d, J=7.2 Hz, 1H), 8.27 (s, 1H), 7.64 (s, 1H), 7.04 (dd, J=1.6, 7.2 Hz, 1H), 4.43 (q, J=7.2 Hz, 2H), 4.31 (m, 2H), 2.87 (m, 1H), 2.83 (m, 2H), 1.95 (m, 2H), 1.67 (m, 2H), 1.49 (s, 9H), 1.43 (t, J=7.2 Hz, 3H). MS m/z 374.2 (M+1)+.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. customthe solvent was evaporated
  3. customto give the crude product
  4. customThe residue was purified over silica

Sources & evidence

ORD record
ord-d7bbdbde8b094ba485d41d3b8d60b23d
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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