Dimethylformamide → N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenyl-1-butyn-1-yl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

HRID 684981Notes

Reaction equation

HRID 684981 reaction equation
[Br:1][c:2]1[cH:3][c:4]2[c:5]([n:6]([CH3:22])[cH:7][c:8]([C:11](=[O:12])[NH:13][CH2:14][c:15]3[cH:16][cH:17][c:18]([Cl:21])[cH:19][cH:20]3)[c:9]2=[O:10])[o:23]1.[CH3:35][CH2:36][N:37]([CH2:38][CH3:39])[CH2:40][CH3:41].[Cu:47][I:48].[O:42]=[CH:43][N:44]([CH3:45])[CH3:46].[Pd:49]([Cl:50])[Cl:51].[c:24]1([CH:30]([CH2:31][C:32]#[CH:33])[OH:34])[cH:25][cH:26][cH:27][cH:28][cH:29]1.[c:52]1([P:53]([c:54]2[cH:55][cH:56][cH:57][cH:58][cH:59]2)[c:60]2[cH:61][cH:62][cH:63][cH:64][cH:65]2)[cH:66][cH:67][cH:68][cH:69][cH:70]1.[c:71]1([P:72]([c:73]2[cH:74][cH:75][cH:76][cH:77][cH:78]2)[c:79]2[cH:80][cH:81][cH:82][cH:83][cH:84]2)[cH:85][cH:86][cH:87][cH:88][cH:89]1>>[c:2]1([C:33]#[C:32][CH2:31][CH:30]([c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[OH:34])[cH:3][c:4]2[c:5]([n:6]([CH3:22])[cH:7][c:8]([C:11](=[O:12])[NH:13][CH2:14][c:15]3[cH:16][cH:17][c:18]([Cl:21])[cH:19][cH:20]3)[c:9]2=[O:10])[o:23]1

Participants

8

Reactant 7

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 10237594HCID 10237594, compoundHCID 110190061-phenylbut-3-yn-1-ol

Product 1

HCID 10195313N-(4-Chlorobenzyl)-2-(4-hydroxy-4-phenyl-1-butyn-1-yl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

Sources & evidence

ORD record
ord-805457e52aa64ac1b0016428818342c5
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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