tert-butyl 7-bromo-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate → tert-Butyl 9-methyl-7-(2-oxo-4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

HRID 2365391Notes

Reaction equation

HRID 2365391 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C:7]=3[N:8]2[CH3:11])=[CH:4][CH:3]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][NH:34][C:33](=[O:37])[CH2:32]1>>[CH3:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([N:34]3[CH2:35][CH2:36][N:31]([CH2:30][CH2:29][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=4)[CH2:32][C:33]3=[O:37])[CH:10]=2)[C:6]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C:7]1=2

Participants

3

Reactant 2

HCID 57950468tert-butyl 7-bromo-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylateHCID 580934314-(2-(Pyridin-2-yl)ethyl)piperazin-2-one

Product 1

HCID 67986817tert-Butyl 9-methyl-7-(2-oxo-4-(2-(pyridin-2-yl)ethyl)piperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylateYield 17.7%

Procedure

tert-Butyl 7-bromo-9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (820 mg, 2.25 mmol) and 4-(2-(pyridin-2-yl)ethyl)piperazin-2-one (426 mg, 2.08 mmol) were reacted according to Example 2 (step f) to provide the title compound (180 mg, 16%) as a yellow oil: ESI MS m/z 490 [M+H]+.

Sources & evidence

ORD record
ord-ab40461999fe4b22add6ad44789a351b
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

Loading…