Formaldehyde → 7-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 1775918Notes

Reaction equation

HRID 1775918 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][C:7]=3[N:8]2CC(C2C=NC(C)=CC=2)O)=[CH:4][CH:3]=1.ClC1C=C(NN)C=CC=1.COC(OC)CCCNC.ClC1C=C2C(C(CCNC)=CN2)=CC=1.C=O>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][C:7]=3[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 712FormaldehydeHCID 75332(3-Chlorophenyl)hydrazineHCID 21071655[2-(6-Chloro-1h-indol-3-yl)ethyl](methyl)amineHCID 22563572(4,4-Dimethoxybutyl)(methyl)amineHCID 442421802-(7-chloro-2-methyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)-1-(6-methylpyridin-3-yl)ethanol

Product 1

HCID 579304787-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Procedure

Method for the preparation of compound 7[[2-(7-chloro-2-methyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)-1-(6-methylpyridin-3-yl)ethanol]: (3-chlorophenyl)hydrazine is reacted with 4,4-dimethoxy-N-methylbutan-1-amine (put in the references for this) to generate 2-(6-chloro-1H-indol-3-yl)-N-methylethanamine, which upon treatment with formaldehyde, under standard Pictet Spingler reaction conditions (insert the reference for this) gives 7-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole. The further reaction of this unsubstituted β-carboline with 2-methyl-5-(oxiran-2-yl)pyridine (carboline, aryl/heteroaryl oxide, NaH, DMF, 120° C.) gives the desired compound 2-(7-chloro-2-methyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)-1-(6-methylpyridin-3-yl)ethanol, compound 7. 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 (insert the reference for this)

Sources & evidence

ORD record
ord-f6b386219c2241f98eaa3e1f4838c369
Source dataset
uspto-grants-2016_02
Patent number
US09260429B2

Reaction notes

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