HCID 67428997, compound → HCID 57744886, compound

HRID 1661498Notes

Reaction equation

HRID 1661498 reaction equation
C([O:5][C:6](=[O:27])[CH2:7][NH:8][C:9]([C:11]1[C:16](=[O:17])[N:15]([CH3:18])[C:14]2[C:19]([CH3:25])=[C:20]([C:22]([OH:24])=[O:23])[S:21][C:13]=2[C:12]=1[OH:26])=[O:10])(C)(C)C.BrC1SC2C(O)=C(C(NCC(OC(C)(C)C)=O)=O)C(=O)N(C)C=2C=1C.[C]=O>CO.[Pd]>[C:6]([CH2:7][NH:8][C:9]([C:11]1[C:16](=[O:17])[N:15]([CH3:18])[C:14]2[C:19]([CH3:25])=[C:20]([C:22]([OH:24])=[O:23])[S:21][C:13]=2[C:12]=1[OH:26])=[O:10])([OH:27])=[O:5]

Participants

6

Reactant 3

HCID 67428997HCID 67428997, compoundHCID 67429401HCID 67429401, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 57744886HCID 57744886, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

6-((2-tert-Butoxy-2-oxoethyl)carbamoyl)-7-hydroxy-3,4-dimethyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-2-carboxylic acid. The title compound is prepared by palladium catalyzed carbonylation of tert-butyl 2-(2-bromo-7-hydroxy-3,4-dimethyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridine-6-carboxamido)acetate with carbon monoxide in MeOH according to the procedure set forth in Tsuji, J. Palladium Reagents and catalysts: Innovations in Organic Synthesis Publisher: (Wiley, Chichester, UK), 340-5 (1995).

Sources & evidence

ORD record
ord-48157223aee94b65a7b5aea6cd83b224
Source dataset
uspto-grants-2011_10
Patent number
US08030346B2

Reaction notes

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