Ethanol → Ethyl 5-[(tert-butoxycarbonyl)amino]-3-chloropyridine-2-carboxylate

HRID 1368262Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[N:11][C:12](Cl)=[C:13]([Cl:15])[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N([CH2:22][CH3:23])CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:54].[CH2:55]([OH:57])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([C:55]([O:57][CH2:22][CH3:23])=[O:54])=[N:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-(N-(tert-butoxycarbonyl)amino)-5,6-dichloropyridine (2.7 g) in anhydrous ethanol (50 ml) were added anhydrous triethylamine (7.38 g), palladium acetate (1.75 g) and 1,3-bis(diphenylphosphino)propane (3.21 g). The inside of the reaction vessel was substituted for 1 atm. carbon monoxide and the mixture was stirred at 60° C. After 10 hr, ethyl acetate (250 ml) was added to the reaction mixture, and an insoluble matter was filtered off. The filtrate was concentrated and the residue was applied to flash silica gel column chromatography (silica gel, 500 ml) and eluted with hexane:ethyl acetate=10:1-5:1-3:1-2:1 to give ethyl 5-(N-(tert-butoxycarbonyl)amino)-3-chloropyridine-2-carboxylate as a colorless solid (5.85 g).

Workup

filtrationan insoluble matter was filtered off
concentrationThe filtrate was concentrated
washeluted with hexane

Sources & evidence

ORD record: ord-514b83fc9fba4511955acb53423f6844
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573274B1

Reaction notes

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