Tetrahydrothiopyran-4-one → 8-Methyl-5-[2-(6-methyl-pyridin-3-yl)-ethyl]-1,3,4,5-tetrahydro-thiopyrano[4,3-b]indole

HRID 2369264Notes

Reaction equation

HRID 2369264 reaction equation
CN1[CH2:24][CH2:23][C:5]2[N:6]([CH2:14][CH2:15][C:16]3[CH:17]=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[S:25]1CCC(=O)CC1>>[CH3:13][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:14][CH2:15][C:16]3[CH:17]=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[C:5]3[CH2:23][CH2:24][S:25][CH2:3][C:4]=3[C:12]=2[CH:11]=1

Participants

3

Reactant 2

HCID 66173Tetrahydrothiopyran-4-oneHCID 197033Latrepirdine

Product 1

HCID 462399138-Methyl-5-[2-(6-methyl-pyridin-3-yl)-ethyl]-1,3,4,5-tetrahydro-thiopyrano[4,3-b]indole

Procedure

The method was the same as for Dimebon, using tetrahydro-thiopyran-4-one in place of 1-methylpiperid-4-one. The desired product was isolated as a glassy yellow oil (13.1 mg, 8.7% over three steps based on 2-methyl-5-(N-nitroso-2-p-tolylaminoethyl)pyridine starting material) by column chromatography on SiO2, eluting with 4:1 EtOAc/MeOH.

Sources & evidence

ORD record
ord-b8506040b9e4495f8cc5e776caa4b12d
Source dataset
uspto-grants-2014_04
Patent number
US08703952B2

Reaction notes

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