Dimethylformamide → 3-[4-(5-Cyanopent-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

HRID 1569641Notes

Reaction equation

HRID 1569641 reaction equation
[C:45]([CH2:46][CH2:47][CH2:48][C:49]#[CH:50])#[N:51].[CH2:21]([NH:22][CH2:23][CH3:24])[CH3:25].[Cu:57][I:58].[I:1][c:2]1[cH:3][cH:4][c:5](-[c:8]2[cH:9][s:10][c:11]3[nH:12][c:13](=[O:20])[c:14]([C:18]#[N:19])[c:15]([OH:17])[c:16]23)[cH:6][cH:7]1.[O:52]=[CH:53][N:54]([CH3:55])[CH3:56].[c:26]1([P:27]([c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[c:34]2[cH:35][cH:36][cH:37][cH:38][cH:39]2)[cH:40][cH:41][cH:42][cH:43][cH:44]1>>[c:2]1([C:50]#[C:49][CH2:48][CH2:47][CH2:46][C:45]#[N:51])[cH:3][cH:4][c:5](-[c:8]2[cH:9][s:10][c:11]3[nH:12][c:13](=[O:20])[c:14]([C:18]#[N:19])[c:15]([OH:17])[c:16]23)[cH:6][cH:7]1

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 1398525-HexynenitrileHCID 546899454-Hydroxy-3-(4-iodophenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 546899353-[4-(5-Cyanopent-1-ynyl)phenyl]-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile

Sources & evidence

ORD record
ord-d3f1ca8923914e8a82bd93c1e87522ab
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (1/10)

Reaction notes

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