Potassium Hydroxide → 3-(8-chloro-5-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)cyclopentanol

HRID 574489ノート

反応式

HRID 574489 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH:15]4[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]4)[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[F:21][C:22]([F:32])([F:31])[C:23]1[CH:28]=[CH:27][C:26]([CH:29]=[CH2:30])=[CH:25][N:24]=1.[OH-].[K+]>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:30][CH2:29][C:26]3[CH:25]=[N:24][C:23]([C:22]([F:32])([F:21])[F:31])=[CH:28][CH:27]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH:15]4[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]4)[CH2:14][C:5]=3[C:4]=2[CH:3]=1

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 574168485-Ethenyl-2-(trifluoromethyl)pyridineHCID 687563083-(8-chloro-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)cyclopentanol

生成物 1

HCID 578758723-(8-chloro-5-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)cyclopentanol

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

3-(8-chloro-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)cyclopentanol (300 mg, 1.03 mmol), 2-trifluoromethyl-5-vinylpyridine (140 mg, 0.809 mmol) and potassium hydroxide (310 mg, 5.5 mmol) in 0.6 ml of NMP was heated to 60 deg C. for 2 h. The reaction mass was cooled at RT and diluted with 20 ml of ethyl acetate. The organic layer was washed with brine and dried over sodium sulphate and concentrated under vacuum. It was purified on 230-400 silica gel (flash) deactivated with triethylamine using ethyl acetate/methanol (5-10%) as eluant, followed by isolation of 3-(8-chloro-5-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2(5H)-yl)cyclopentanol by PREP HPLC. Yield: 70 mg as TFA salt.

後処理

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated under vacuum
  4. customIt was purified on 230-400 silica gel (flash)

出典と根拠

ORDレコード
ord-d461d35457fb4efa9dfd80e09a9e697b
出典データセット
uspto-grants-2015_05
特許番号
US09034880B2

反応ノート

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