Propargyl alcohol → N-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxyprop-1-ynyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

HRID 174397Notes

Reaction equation

HRID 174397 reaction equation
[CH2:25]([C:26]#[CH:27])[OH:28].[CH2:29]([NH:30][CH2:31][CH3:32])[CH3:33].[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][C:8](=[O:9])[c:10]2[c:11](=[O:22])[c:12]3[c:13]([n:14]([CH2:16][CH3:17])[cH:15]2)[s:18][c:19]([I:21])[cH:20]3)[cH:23][cH:24]1.[Cu:34]([I:35])[I:36].[Pd:37]([Cl:38])[Cl:39].[c:40]1([P:41]([c:42]2[cH:43][cH:44][cH:45][cH:46][cH:47]2)[c:48]2[cH:49][cH:50][cH:51][cH:52][cH:53]2)[cH:54][cH:55][cH:56][cH:57][cH:58]1.[c:59]1([P:60]([c:61]2[cH:62][cH:63][cH:64][cH:65][cH:66]2)[c:67]2[cH:68][cH:69][cH:70][cH:71][cH:72]2)[cH:73][cH:74][cH:75][cH:76][cH:77]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][C:8](=[O:9])[c:10]2[c:11](=[O:22])[c:12]3[c:13]([n:14]([CH2:16][CH3:17])[cH:15]2)[s:18][c:19]([C:27]#[C:26][CH2:25][OH:28])[cH:20]3)[cH:23][cH:24]1

Participants

7

Reactant 6

HCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 83717Copper iodideHCID 9847660HCID 9847660, compound

Product 1

HCID 6483693N-[(4-chlorophenyl)methyl]-7-ethyl-2-(3-hydroxyprop-1-ynyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

Sources & evidence

ORD record
ord-afd9a71325fe4657920c740f494281fe
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (9/10)

Reaction notes

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