3-(1,2,3,5,8,8a-Hexahydro-7-indolizinyl)-1H-6-azaindole → 3-(1-Methyl-4-piperidinyl)-5-azaindole

HRID 2119568Notes

Reaction equation

HRID 2119568 reaction equation
C1[CH:9]2[N:4]([CH2:5][CH2:6][CH:7]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:8]2)[CH2:3]C1.C1C2N(CC=C(C3C4C(=CN=CC=4)NC=3)C2)CC1>C(O)C.[Pd]>[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:17](=[CH:16][CH:15]=[N:14][CH:13]=3)[NH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 98812273-(1,2,3,5,8,8a-Hexahydro-7-indolizinyl)-1H-6-azaindoleHCID 102204153-(octahydro-7-indolizinyl)-1H-7-azaindole

Product 1

HCID 101306073-(1-Methyl-4-piperidinyl)-5-azaindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(Octahydro-7-indolizinyl)-1H-7-azaindole (less polar isomer 134.2 mg, 49.5% and more polar isomer 36.6 mg, 13.3%); from 3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-6-azaindole (270 mg, 1.13 mmol) and 10% Pd/C (300 mg) in ethanol (4 mL) under H2 overnight.

Workup

  1. customovernight

Sources & evidence

ORD record
ord-5494ec2f19ff45158d8f331c78dfa072
Source dataset
uspto-grants-2004_02
Patent number
US06686374B1

Reaction notes

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