Formaldehyde → 6-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 2198298Notes

Reaction equation

HRID 2198298 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.COC(OC)CCCNC.ClC1C=[C:23]2[C:27](=CC=1)NC=[C:24]2[CH2:30][CH2:31][NH:32][CH3:33].C=O>>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:8][C:23]1[CH2:27][N:32]([CH3:33])[CH2:31][CH2:30][C:24]2=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 70624(4-Chlorophenyl)hydrazineHCID 22563572(4,4-Dimethoxybutyl)(methyl)amineHCID 57825686HCID 57825686, compound

Product 1

HCID 155083736-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Procedure

Method for the synthesis of compound 6 [6-chloro-2-methyl-9-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole]: (4-chlorophenyl)hydrazine is reacted with 4,4-dimethoxy-N-methylbutan-1-amine (Phytochemistry 1985, 24 (8), 1653-1656) to generate 2-(5-chloro-1H-indol-3-yl)-N-methylethanamine which upon treatment with formaldehyde, under standard Pictet Spingler reaction conditions (U.S. Pat. No. 2,642,438) gives 6-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole. The further reaction of this unsubstituted β-carboline with 2-(trifluoromethyl)-5-vinylpyridine gives the desired compound [6-chloro-2-methyl-9-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole], compound 6. After the successful synthesis of the compound, purification can be achieved using standard normal phase or reverse phase methods.

Workup

  1. customunder standard Pictet Spingler reaction conditions (U.S

Sources & evidence

ORD record
ord-289cd4118e79423e8f03b47a1527c70f
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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