Dimethylformamide → 5-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-nicotinonitrile

HRID 176398Notes

Reaction equation

HRID 176398 reaction equation
[CH2:17]([CH2:18][C:19]#[CH:20])[c:21]1[cH:22][cH:23][c:24]([CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)[cH:31][cH:32]1.[CH3:33][CH2:34][N:35]([CH2:36][CH3:37])[CH2:38][CH3:39].[Cl:1][c:2]1[c:3]([C:4]#[N:5])[cH:6][c:7](-[c:10]2[cH:11][cH:12][c:13]([Cl:16])[cH:14][cH:15]2)[cH:8][n:9]1.[Cu:45][I:46].[O:40]=[CH:41][N:42]([CH3:43])[CH3:44].[Pd:47]([Cl:48])[Cl:49].[c:50]1([P:51]([c:52]2[cH:53][cH:54][cH:55][cH:56][cH:57]2)[c:58]2[cH:59][cH:60][cH:61][cH:62][cH:63]2)[cH:64][cH:65][cH:66][cH:67][cH:68]1.[c:69]1([P:70]([c:71]2[cH:72][cH:73][cH:74][cH:75][cH:76]2)[c:77]2[cH:78][cH:79][cH:80][cH:81][cH:82]2)[cH:83][cH:84][cH:85][cH:86][cH:87]1>>[c:2]1([C:20]#[C:19][CH2:18][CH2:17][c:21]2[cH:22][cH:23][c:24]([CH2:25][N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[cH:31][cH:32]2)[c:3]([C:4]#[N:5])[cH:6][c:7](-[c:10]2[cH:11][cH:12][c:13]([Cl:16])[cH:14][cH:15]2)[cH:8][n:9]1

Participants

8

Reactant 7

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 27640422-Chloro-5-(4-chlorophenyl)nicotinonitrileHCID 859698431-(4-But-3-ynyl-benzyl)-pyrrolidine

Product 1

HCID 100025565-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-nicotinonitrile

Sources & evidence

ORD record
ord-63c3900bdda8449e8f53b4962d93ea4f
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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