1-Methylindole-3-carboxylic acid → (cis-7-Methoxy-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinolin-4-yl)-(1-methyl-1H-indol-3-yl)-methanone

HRID 2272070Notes

Reaction equation

HRID 2272070 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[CH:3]1.[CH3:14][O:15][C:16]1[C:29]2[CH2:28][CH2:27][C@H:26]3[C@H:21]([CH2:22][CH2:23][CH2:24][NH:25]3)[C:20]=2[CH:19]=[CH:18][CH:17]=1>>[CH3:14][O:15][C:16]1[C:29]2[CH2:28][CH2:27][C@H:26]3[C@H:21]([CH2:22][CH2:23][CH2:24][N:25]3[C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[O:13])[C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 8540401-Methylindole-3-carboxylic acidHCID 86654085cis-7-Methoxy-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline

Product 1

HCID 86654119(cis-7-Methoxy-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinolin-4-yl)-(1-methyl-1H-indol-3-yl)-methanoneYield 82%

Procedure

The title compound is prepared from 1-methyl-1H-indole-3-carboxylic acid and cis-7-methoxy-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline following a procedure analogous to that described in Example 1. Yield: 82% of theory; LC (method 1): tR=4.39 min; Mass spectrum (ESI+): m/z=375 [M+H]+.

Sources & evidence

ORD record
ord-d74acc15c9594f64bd6427f8416545aa
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

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