Dimethylformamide → 5-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole-2,3-dione

HRID 196364Notes

Reaction equation

HRID 196364 reaction equation
[CH2:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)[CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]#[CH:17])[CH2:12][CH2:13]1.[CH3:18][CH2:19][N:20]([CH2:21][CH3:22])[CH2:23][CH3:24].[Cu:42][I:43].[I:25][c:26]1[cH:27][c:28]2[c:32]([cH:33][cH:34]1)[NH:31][C:30](=[O:35])[C:29]2=[O:36].[O:37]=[CH:38][N:39]([CH3:40])[CH3:41].[Pd:44]([Cl:45])[Cl:46].[c:47]1([P:48]([c:49]2[cH:50][cH:51][cH:52][cH:53][cH:54]2)[c:55]2[cH:56][cH:57][cH:58][cH:59][cH:60]2)[cH:61][cH:62][cH:63][cH:64][cH:65]1.[c:66]1([P:67]([c:68]2[cH:69][cH:70][cH:71][cH:72][cH:73]2)[c:74]2[cH:75][cH:76][cH:77][cH:78][cH:79]2)[cH:80][cH:81][cH:82][cH:83][cH:84]1>>[CH2:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)[CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]#[C:17][c:26]2[cH:27][c:28]3[c:32]([cH:33][cH:34]2)[NH:31][C:30](=[O:35])[C:29]3=[O:36])[CH2:12][CH2:13]1

Participants

8

Reactant 7

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 886955-IodoisatinHCID 106093551-(3-Butynyl)-4-benzylpiperidine

Product 1

HCID 107618245-[4-(4-Benzyl-piperidin-1-yl)-but-1-ynyl]-1H-indole-2,3-dione

Sources & evidence

ORD record
ord-bc99119fd3834530a7594ec9caf162e9
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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