Potassium Carbonate → tert-Butyl 5-methyl-7-(2-oxo-4-((5-(trifluoromethyl)pyridin-2-yl)methoxy)pyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 930713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 930713
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1.[OH:13][C:14]1[CH:19]=[CH:18][N:17]([C:20]2[CH:21]=[CH:22][C:23]3[C:24]4[CH2:33][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31][CH2:30][C:25]=4[N:26]([CH3:29])[C:27]=3[CH:28]=2)[C:16](=[O:41])[CH:15]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CN(C=O)C.C(Cl)Cl>[CH3:29][N:26]1[C:27]2[CH:28]=[C:20]([N:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:2][C:3]4[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=4)=[CH:15][C:16]3=[O:41])[CH:21]=[CH:22][C:23]=2[C:24]2[CH2:33][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:31][CH2:30][C:25]1=2

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 214410942-(Bromomethyl)-5-(trifluoromethyl)pyridineHCID 68657574tert-butyl 7-(4-hydroxy-2-oxopyridin-1(2H)-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Produkt 1

HCID 57950385tert-Butyl 5-methyl-7-(2-oxo-4-((5-(trifluoromethyl)pyridin-2-yl)methoxy)pyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21891449acetonitrile N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

2-(Bromomethyl)-5-(trifluoromethyl)pyridine (140 mg, 0.58 mmol), tert-butyl 7-(4-hydroxy-2-oxopyridin-1(2H)-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (230 mg, 0.58 mmol) and K2CO3 (160 mg, 1.16 mmol) were stirred in acetonitrile/DMF (3 mL/0.5 mL) for 72 h. The mixture was diluted with methylene chloride, washed with water and concentrated to provide the title compound (96 mg, 29%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.88 (s, 1H), 8.00 (dd, J=8.2, 2.0 Hz, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.51 (d, J=8.2 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H), 7.28-7.26 (m, 1H), 7.00 (d, J=7.7 Hz, 1H), 6.12 (dd, J=7.6, 2.7 Hz, 1H), 6.04 (d, J=2.7 Hz, 1H), 5.26 (s, 2H), 4.63-4.58 (br m, 2H), 3.87-3.76 (br m, 2H), 3.63 (s, 3H), 2.86-2.76 (br m, 2H), 1.50 (s, 9H).

Aufarbeitung

  1. washwashed with water
  2. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-329062828a1f4719982a1a0286aa4fda
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296743B2

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