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

HRID 2198300
ノート
印刷プレビュー

反応式

HRID 2198300 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6f4c0a070d96472fbff70f4473f5b0ae
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08338447B2

反応ノート

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