Acetate → 4-Hydroxy-3-(2'-hydroxy-biphenyl-4-yl)-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

HRID 184114Notes

Reaction equation

HRID 184114 reaction equation
[CH2:1]([CH3:2])[O:3][C:4](=[O:5])[c:6]1[c:7]([OH:23])[c:8]2[c:9]([nH:10][c:11]1=[O:12])[s:13][cH:14][c:15]2-[c:16]1[cH:17][cH:18][c:19]([Br:22])[cH:20][cH:21]1.[CH2:42]1[O:43][CH2:44][CH2:45][CH2:46]1.[K+:39].[K+:40].[K+:41].[O-:48][C:49]([CH3:50])=[O:51].[O-:52][C:53]([CH3:54])=[O:55].[OH2:56].[OH:24][c:25]1[c:26]([B:31]([OH:32])[OH:33])[cH:27][cH:28][cH:29][cH:30]1.[P:34]([O-:35])([O-:36])([O-:37])=[O:38].[Pd+2:47]>>[CH2:1]([CH3:2])[O:3][C:4](=[O:5])[c:6]1[c:7]([OH:23])[c:8]2[c:9]([nH:10][c:11]1=[O:12])[s:13][cH:14][c:15]2-[c:16]1[cH:17][cH:18][c:19](-[c:26]2[c:25]([OH:24])[cH:30][cH:29][cH:28][cH:27]2)[cH:20][cH:21]1

Participants

9

Reactant 8

HCID 175Acetate2×HCID 813Potassium Cation3×HCID 962WaterHCID 1061PhosphateHCID 8028TetrahydrofuranHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 2773454(2-Hydroxyphenyl)boronic acidHCID 547275683-(4-Bromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 546898724-Hydroxy-3-(2'-hydroxy-biphenyl-4-yl)-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

Sources & evidence

ORD record
ord-4919fd08e3644217a7086daac4bc6ead
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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