proline dl-form → 9-Chloro-3-methyl-6-(2-pyridin-4-ylprop-1-enyl)-1,2,4,5-tetrahydroazepino[4,5-b]indole

HRID 155385Notes

Reaction equation

HRID 155385 reaction equation
[Br:17][CH:18]=[C:19]([CH3:20])[c:21]1[cH:22][cH:23][n:24][cH:25][cH:26]1.[Cl:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]([nH:7][c:8]2[cH:9][cH:10]1)[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3.[Cu:47][I:48].[F:35][C:36]([F:37])([F:38])[C:39]([OH:40])=[O:41].[O:42]=[CH:43][N:44]([CH3:45])[CH3:46].[OH2:49].[OH:27][C:28]([CH:29]1[NH:30][CH2:31][CH2:32][CH2:33]1)=[O:34]>>[Cl:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]([n:7]([CH:18]=[C:19]([CH3:20])[c:21]4[cH:22][cH:23][n:24][cH:25][cH:26]4)[c:8]2[cH:9][cH:10]1)[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]3

Participants

8

Reactant 7

HCID 614proline dl-formHCID 962WaterHCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 685585079-Chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indoleHCID 86642478(E)-4-(1-bromoprop-1-en-2-yl)pyridine

Product 1

HCID 685600709-Chloro-3-methyl-6-(2-pyridin-4-ylprop-1-enyl)-1,2,4,5-tetrahydroazepino[4,5-b]indole

Sources & evidence

ORD record
ord-c6067ceff038429fae9404fa32c05af0
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (9/10)

Reaction notes

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