Methanol → HCID 9837669, compound

HRID 895448Notes

Reaction equation

HRID 895448 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH:6]=[C:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[N:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1.CO>C(O)C.ClCCl.[Pd]>[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[N:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 887MethanolHCID 101309743-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole

Product 1

HCID 9837669HCID 9837669, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole (400 mg, 1.67 mmol) and 10%Pd/C (400 mg) in ethanol (15 mL) was stirred under H2 overnight. The reaction mixture was filtered and the filtrate concentrated and purified by column chromatography. Elution with 5% methanol (2M/NH3) in dichloromethane gave the less polar isomer (297.7 mg, 73.5%) and with 10% methanol (2M/NH3) in dichloromethane gave the more polar isomer (73 mg, 18.1%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. custompurified by column chromatography
  4. washElution with 5% methanol (2M/NH3) in dichloromethane
  5. customgave the less polar isomer (297.7 mg, 73.5%)

Sources & evidence

ORD record
ord-f6c2a88243924f72b89f699628380378
Source dataset
uspto-grants-2005_07
Patent number
US06916818B2

Reaction notes

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