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 2195933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2195933
[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

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-59b5890dc15c47088ff462d858af2f3b
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338408B2

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