Ethyl 3-(3-chlorophenyl)prop-2-ynoate → 7-(2-{1-[1-(3-Chloro-phenyl)-2-ethoxycarbonyl-vinyl]-1H-indol-5-yloxy}-ethyl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[CH3:2].[C:15]([O:19][C:20]([N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][CH2:33][O:34][C:35]3[CH:36]=[C:37]4[C:41](=[CH:42][CH:43]=3)[NH:40][CH:39]=[CH:38]4)[N:30]=2)[CH2:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>>[C:15]([O:19][C:20]([N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][CH2:33][O:34][C:35]3[CH:36]=[C:37]4[C:41](=[CH:42][CH:43]=3)[N:40]([C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=3)=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH:39]=[CH:38]4)[N:30]=2)[CH2:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]Participants
3
Reactant 2
Product 1
Procedure
The title compound was synthesized from (3-chloro-phenyl)-propynoic acid ethyl ester and 7-[2-(1H-Indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester using the procedure described in Example 16, step (d1), in 90% yield as an E/Z isomeric mixture. 1H NMR (CDCl3) [E/Z mixture] δ 7.36-7.24 (m, 2H), 7.14-7.6.70 (m, 8H), 6.56 (s, 0.5H), 6.48 (m, 0.5H), 6.21 (s, 0.5H), 6.14 (s, 0.5H), 4.37 (m, 2H), 4.12 (q, 2H, J=6.8 Hz), 3.76 (m, 2H), 3.20 (t, 2H, J=6.8 Hz), 2.73 (t, 2H, J=6.8 Hz), 1.92 (m, 2H), 1.52 (s, 9H), 1.26 (t, 3H, J=7.2 Hz). Mass Spectrum (LCMS, ESI) calculated for C29H29ClN3O3 502.2 (M-Boc+1); found 502.4.
Sources & evidence
- ORD record
- ord-817d9f133c9f4e13b2c4e0828f444f10
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855722B2
Reaction notes
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