Toluene → 1-(2-Diethylaminoethyl)-4-bromo-6-[3-(2-oxo-1-imidazolidinyl)-1-propynyl]-3-hydroxy-3-(2-chlorophenyl)oxindole
Reaction equation
[CH2:1]([CH3:2])[N:3]([CH2:4][CH2:5][N:6]1[C:7](=[O:25])[C:8]([c:17]2[c:18]([Cl:23])[cH:19][cH:20][cH:21][cH:22]2)([OH:24])[c:9]2[c:10]([Br:16])[cH:11][c:12]([I:15])[cH:13][c:14]21)[CH2:26][CH3:27].[CH2:94]1[O:95][CH2:96][CH2:97][CH2:98]1.[CH3:37][CH2:38][N:39]([CH2:40][CH3:41])[CH2:42][CH3:43].[CH3:44][c:45]1[cH:46][cH:47][cH:48][cH:49][cH:50]1.[Cu:92][I:93].[O:28]=[C:29]1[N:30]([CH2:34][C:35]#[CH:36])[CH2:31][CH2:32][NH:33]1.[Pd:51]([Cl:52])[Cl:53].[c:54]1([P:55]([c:56]2[cH:57][cH:58][cH:59][cH:60][cH:61]2)[c:62]2[cH:63][cH:64][cH:65][cH:66][cH:67]2)[cH:68][cH:69][cH:70][cH:71][cH:72]1.[c:73]1([P:74]([c:75]2[cH:76][cH:77][cH:78][cH:79][cH:80]2)[c:81]2[cH:82][cH:83][cH:84][cH:85][cH:86]2)[cH:87][cH:88][cH:89][cH:90][cH:91]1>>[CH2:1]([CH3:2])[N:3]([CH2:4][CH2:5][N:6]1[C:7](=[O:25])[C:8]([c:17]2[c:18]([Cl:23])[cH:19][cH:20][cH:21][cH:22]2)([OH:24])[c:9]2[c:10]([Br:16])[cH:11][c:12]([C:36]#[C:35][CH2:34][N:30]3[C:29](=[O:28])[NH:33][CH2:32][CH2:31]3)[cH:13][c:14]21)[CH2:26][CH3:27]Participants
9
Reactant 8
HCID 1140Toluene
HCID 8028Tetrahydrofuran
HCID 8471Triethylamine
HCID 11776Triphenylphosphine2×
HCID 24290Palladium Chloride
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
HCID 156696571-(Prop-2-yn-1-yl)imidazolidin-2-one
HCID 185186541-(2-Diethylaminoethyl)-3-hydroxy-3-(2-chlorophenyl)-4-bromo-6-iodooxindoleProduct 1
Sources & evidence
- ORD record
- ord-f9da1e10743043b5a96954c87544ed59
- Source dataset
- Validation data from https://doi.org/10.1039/C8SC04228D
Reaction notes
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