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

HRID 2198300
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HRID 2198300 반응식
[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
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참가 물질

6

반응물 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

생성물 1

HCID 57930478
7-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

실험 절차

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.

후처리

  1. customunder standard Pictet Spingler reaction conditions (insert the reference for this)

출처 및 근거

ORD 기록
ord-6f4c0a070d96472fbff70f4473f5b0ae
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08338447B2

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