4-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one → 4-(4-Chlorobenzyloxy)-1-(2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridin-2(1H)-one hydrochloride

HRID 1020558Notes

Reaction equation

HRID 1020558 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:26]=[C:25]2[C:21]([C:22]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][C:23]=3[N:24]2[CH3:27])=[CH:20][CH:19]=1>>[ClH:1].[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:18]3[CH:26]=[C:25]4[C:21]([C:22]5[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][C:23]=5[N:24]4[CH3:27])=[CH:20][CH:19]=3)[C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 579503597-Bromo-2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Product 1

HCID 686575774-(4-Chlorobenzyloxy)-1-(2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridin-2(1H)-one hydrochlorideYield 35%

Procedure

4-(4-Chlorobenzyloxy)pyridin-2(1H)-one (82 mg, 0.34 mmol) and 7-bromo-2,9-dimethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (97 mg, 0.34 mmol) were reacted following the procedure for Example 30 (step g) to provide the title compound (28 mg, 17%) as a yellow solid: mp 290-296° C.; 1H NMR (500 MHz, CD3OD) δ 7.83 (d, J=7.6 Hz, 1H), 7.68 (d, J=8.3 Hz, 1H), 7.50-7.46 (m, 3H), 7.44-7.42 (m, 2H), 7.08 (dd, J=8.3, 1.8 Hz, 1H), 6.41 (dd, J=7.6, 2.6 Hz, 1H), 6.21 (d, J=2.6 Hz, 1H), 5.21 (s, 2H), 4.86-4.84 (m, 1H), 4.49 (d, J=15.4 Hz, 1H), 3.88-3.84 (m, 1H), 3.72 (s, 3H), 3.55-3.50 (m, 1H), 3.21-3.16 (m, 5H); ESI MS m/z 434 [M+H]; HPLC (Method B) 98.6% (AUC), tR=14.0 min.

Sources & evidence

ORD record
ord-d1c4954775a64b18ac7970d8e0907108
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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