1-(2-Bromoethyl)piperidine → 2-Tert-butoxy-2-[4-(4-chlorophenyl)-6-methyl-7-oxo-1-[2-(1-piperidyl)ethyl]pyrrolo[2,3-c]pyridin-5-yl]acetic acid
Reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[NH:19][CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>>[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[N:19]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in a manner similar to that described in Example 2 from methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate and 1-(2-bromoethyl)piperidine. 1H NMR (400 MHz, METHANOL-d4) ppm 7.62-7.52 (m, 3H), 7.48-7.41 (m, 1H), 7.39-7.31 (m, 1H), 6.09-6.03 (m, 1H), 5.27 (s, 1H), 5.00-4.91 (m, 2H), 3.75 (s, 3H), 3.68-3.53 (m, 4H), 3.12-2.95 (m, 2H), 2.04-1.92 (m, 2H), 1.92-1.75 (m, 2H), 1.62-1.46 (m, 2H), 0.96 (s, 9H); LCMS (m/z) ES+=500 (M+1).
Sources & evidence
- ORD record
- ord-8c98092c59744b4b859db1fb96f3e601
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012642B2
Reaction notes
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