HCID 59455235, compound → HCID 57875913, compound

HRID 509707Notes

Reaction equation

HRID 509707 reaction equation
[CH3:1][N:2]1[CH2:24][CH2:23][C:5]2[N:6]([CH2:14][C:15]#[C:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[H][H]>CO.[Pd]>[CH3:1][N:2]1[CH2:24][CH2:23][C:5]2[N:6]([CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

5

Reactant 2

HCID 59455235HCID 59455235, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57875913HCID 57875913, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,3,4,5-tetrahydro-2,8-dimethyl-5-(3-(pyridin-2-yl)prop-2-ynyl)-1H-pyrido[4,3-b]indole (See Example 61A) (20 mg, 0.06 mmol) was hydrogenated in methanol (2 ml) with 10% Pd—C (10 mg) at 1 atm of hydrogen to obtain 5 mg of 2,3,4,5-tetrahydro-2,8-dimethyl-5-(3-(pyridin-2-yl)propyl)-1H-pyrido[4,3-b]indole after purification on neutral alumina chromatography eluting with methanol-dichloromethane gradient. The free base was converted into its diHCl salt by treatment of ethanolic HCl.

Sources & evidence

ORD record
ord-f7f7011f8d93412a90ccfdba6119c0a9
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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