proline dl-form → 6-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

HRID 2162723Notes

Reaction equation

HRID 2162723 reaction equation
[C:40](=[O:41])([O-:42])[O-:43].[CH3:25][O:26][C:27](=[O:28])[c:29]1[cH:30][n:31]([CH3:39])[c:32]2[cH:33][c:34]([Br:38])[cH:35][cH:36][c:37]12.[CH3:54][S:55](=[O:56])[CH3:57].[CH:1]1([c:4]2[c:5]([CH2:17][O:18][CH:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[c:6](-[c:9]3[c:10]([Cl:16])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[n:7][o:8]2)[CH2:2][CH2:3]1.[Cu:58][I:59].[K+:44].[K+:45].[OH:46][C:47]([CH:48]1[NH:49][CH2:50][CH2:51][CH2:52]1)=[O:53]>>[CH:1]1([c:4]2[c:5]([CH2:17][O:18][CH:19]3[CH2:20][CH2:21][N:22]([c:34]4[cH:33][c:32]5[n:31]([CH3:39])[cH:30][c:29]([C:27]([O:26][CH3:25])=[O:28])[c:37]5[cH:36][cH:35]4)[CH2:23][CH2:24]3)[c:6](-[c:9]3[c:10]([Cl:16])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[n:7][o:8]2)[CH2:2][CH2:3]1

Participants

8

Reactant 7

HCID 614proline dl-formHCID 679Dimethyl SulfoxideHCID 813Potassium Cation2×HCID 19660Carbonate IonHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 57443279Methyl 6-bromo-1-methyl-1H-indole-3-carboxylateHCID 593693344-{[5-Cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazol-4-yl]methoxy}piperidine

Product 1

HCID 593693306-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-piperidin-1-yl}-1-methyl-1H-indole-3-carboxylic acid methyl ester

Sources & evidence

ORD record
ord-9fa2e65fec9e4a98ad150e0d07a78cfb
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (4/10)

Reaction notes

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