4-Fluorophenylboronic acid → Methyl 1-(4-fluorophenyl)-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 347567Notes

Reaction equation

HRID 347567 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:7](=[O:10])[NH:8][CH:9]=1)([O-:3])=[O:2].[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>N1C=CC=CC=1.O1CCOCC1.N.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:8]2[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:7]2=[O:10])=[CH:18][CH:17]=1

Participants

7

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 7204882Methyl 2-hydroxy-5-nitronicotinate

Product 1

HCID 21081724Methyl 1-(4-fluorophenyl)-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylateYield 52.3%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 222AmmoniaSolventHCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylate (850 mg, 4.29 mmol), 4-fluorophenylboronic acid (1.40 g, 10 mmol, Combi-Blocks) and copper acetate (200 mg, 1.1 mmol) in pyridine (1 mL) and dioxane (20 mL) was stirred at 80° C. for 4 h. The reaction mixture was cooled to room temperature and diluted with a solution of ammonia. The solid was collected, washed with water and dried to afford the title compound (656 mg, 52%). 1H NMR (DMSO-d6) δ 8.95 (d, 1H, J=3.2 Hz), 8.80 (d, 1H, J=3.2 Hz), 7.40 (m, 2H), 7.25 (m, 2H), 3.95 (s, 3H); MS(ESI+) m/z 293 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solid was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-374bb6ae065c4439b4328520762d9d41
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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