Potassium Carbonate → Ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-3-furoate

HRID 537061Notes

Reaction equation

Br[C:2]1[O:6][CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1.[CH3:12][C:13]1[C:14](B2OC(C)(C)C(C)(C)O2)=[CH:15][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[N:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O.C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:20]([NH:19][C:16]1[CH:15]=[C:14]([C:2]2[O:6][CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=2)[C:13]([CH3:12])=[CH:18][N:17]=1)(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 5-bromo-3-furoate (23.7 g, 108.9 mmol), N-[5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-yl]acetamide (20.0 g, 72.5 mmol), Pd(dppf)Cl2 (5.92 g, 9.09 mmol) and K2CO3 (20.0 g, 72.5 mmol) in water (72.5 mL) and toluene (1240 mL) was allowed to stir at 100° C. under an atmosphere of nitrogen overnight. The mixture was filtered while hot and then concentrated. The residue was washed with EtOH and water and then dried to give ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-3-furoate (20.0 g, 67%).

Workup

filtrationThe mixture was filtered while hot and
concentrationthen concentrated
washThe residue was washed with EtOH and water
customdried

Sources & evidence

ORD record: ord-061e3c02a7994001a21a0ec0fca3d728
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859768B2

Reaction notes

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