Water → 2-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(4-chlorophenyl)ethanone

HRID 1773247노트

반응식

HRID 1773247 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+].Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[O:21].O>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[O:21])[C:6]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 68303p-Chlorophenacyl bromide

생성물 1

HCID 497793092-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-1-(4-chlorophenyl)ethanone

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

8-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (220 mg, 1 mmol) was dissolved in 2 mL NMP and to this was added KOH (560 mg, 10 mmol) followed by 2-bromo-1-(4-chloro-phenyl)-ethanone (233 mg, 1 mmol) The reaction was kept overnight at RT. Water was added and the compound extracted with EtOAc. The organic layer was washed with water, concentrated and purified by column chromatography using silica gel (#100-200 mesh) using 0-3% MeOH:DCM as eluent. The compound was further purified by reverse phase chromatography. 1HNMR (CD3OD, TFA salt) d (ppm): 8.10 (m, 2H), 7.60 (d, 2H), 7.50 (s, 1H), 7.30 (d, 1H), 7.10 (m, 1H), 5.80 (m, 2H), 4.70 (m, 1H), 4.40 (m, 1H), 3.80 (m, 1H), 3.60 (m, 1H), 3.05 (s, 5H).

후처리

  1. extractionthe compound extracted with EtOAc
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. custompurified by column chromatography
  5. customThe compound was further purified by reverse phase chromatography

출처 및 근거

ORD 기록
ord-01dff0510a1549a2a992733426fb8b3c
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255094B2

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