7-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester → 7-{2-[1-(1-Biphenyl-4-yl-2-ethoxycarbonyl-vinyl)-1H-indol-5-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

HRID 24010Notes

Reaction equation

HRID 24010 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[NH:26][CH:25]=[CH:24]4)[N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:30]([O:32][C:33](=[O:49])[CH:34]=[C:35]([C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:39][CH:38]=1)Cl)[CH3:31]>>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([C:35]([C:37]3[CH:38]=[CH:39][C:40]([C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)=[CH:41][CH:42]=3)=[CH:34][C:33]([O:32][CH2:30][CH3:31])=[O:49])[CH:25]=[CH:24]4)[N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 668210837-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl esterHCID 865864043-Biphenyl-4-yl-3-chloro-acrylic acid ethyl ester

Product 1

HCID 668213087-{2-[1-(1-Biphenyl-4-yl-2-ethoxycarbonyl-vinyl)-1H-indol-5-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl esterYield 8%

Procedure

The title compound was synthesized from 7-[2-(1H-indol-5-yloxy)-ethyl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester and 3-biphenyl-4-yl-3-chloro-acrylic acid ethyl ester using the procedure described in Example 18, step (d), in an 8% yield as a mixture of E/Z isomers.

Workup

  1. additiondescribed in Example 18, step (d), in an 8% yield as a mixture of E/Z isomers

Sources & evidence

ORD record
ord-6ed0a590d3c8457395966c04bdee1df8
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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