4-((6-(Trifluoromethyl)pyridin-3-yl)methoxy)pyridin-2(1H)-one → tert-Butyl 5-methyl-7-(2-oxo-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 1020627Notes

Reaction equation

HRID 1020627 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[CH:12]=2)=[CH:5][CH:4]=1.Br[C:21]1[CH:22]=[CH:23][C:24]2[C:25]3[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:32][CH2:31][C:26]=3[N:27]([CH3:30])[C:28]=2[CH:29]=1>>[CH3:30][N:27]1[C:28]2[CH:29]=[C:21]([N:14]3[CH:15]=[CH:16][C:11]([O:10][CH2:9][C:6]4[CH:7]=[N:8][C:3]([C:2]([F:1])([F:18])[F:19])=[CH:4][CH:5]=4)=[CH:12][C:13]3=[O:17])[CH:22]=[CH:23][C:24]=2[C:25]2[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:32][CH2:31][C:26]1=2

Participants

3

Reactant 2

HCID 579503604-((6-(Trifluoromethyl)pyridin-3-yl)methoxy)pyridin-2(1H)-oneHCID 57950375tert-Butyl 7-bromo-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 57950450tert-Butyl 5-methyl-7-(2-oxo-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 40.1%

Procedure

4-((6-(Trifluoromethyl)pyridin-3-yl)methoxy)pyridin-2(1H)-one (177 mg, 0.655 mmol) and tert-butyl 7-bromo-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (200 mg, 0.54 mmol) were reacted following the procedure of Example 30 (step g) to provide the title compound (120 mg, 40%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 8.80 (s, 1H), 7.95 (d, J=8.1 Hz, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.51 (d, J=7.9 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.28 (m, 1H), 7.01 (d, J=8.1 Hz, 1H), 6.06-6.04 (m, 2H), 5.16 (s, 2H), 4.65-4.60 (br m, 2H), 3.89-3.79 (br m, 2H), 3.63 (s, 3H), 2.87-2.78 (br m, 2H), 1.50 (s, 9H).

Sources & evidence

ORD record
ord-69c47270d88b4de1b7dcc2185f1f6a2c
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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