HCID 18511245, compound → HCID 9817266, compound

HRID 1371124Notes

Reaction equation

HRID 1371124 reaction equation
[C:1]1([C:7]2[NH:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:7]2[NH:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[N:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 18511245HCID 18511245, compound

Product 1

HCID 9817266HCID 9817266, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Cyclohex-1-enyl-7-piperidylpyrrolo[3,2-b]pyridine (Example 43(b)) (280 mg, 1 mmol) was dissolved in MeOH (5 mL), and 10% palladium on charcoal (28 mg) was added. The flask was purged with H2 and a doubled-walled balloon filled with H2 was attached to the flask (˜30 psi H2). After 16 h, the mixture was filtered through celite, and the filtrate was concentrated in vacuo. The crude material was purified by flash chromatography 1:9 MeOH:EtOAc to afford 0.28 g (99%) of the title compound as an off-white solid. 1H NMR (DMSO-d6; 500 MHz): δ 2.0-1.2 (m, 16), 2.72 (m, 1), 3.18 (t, 4, J=5.2), 6.22 (s, 1), 6.55 (d, 1, J=5.3), 8.04 (d, 1, J=5.3), 10.61 (s, 1). MS m/z: 284 (M+1). Anal. Calcd for C18H25N3O.0.2H20: C, 75.33; H, 8.92; N, 14.64. Found: C, 75.39; H, 8.64; N, 14.64.

Workup

  1. customThe flask was purged with H2
  2. additiona doubled-walled balloon filled with H2
  3. filtrationthe mixture was filtered through celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude material was purified by flash chromatography 1:9 MeOH

Sources & evidence

ORD record
ord-69484a8f994c4aaab86cf9c52fe30f38
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

Loading…