Pyridine → HCID 68083398, compound

HRID 711278Notes

Reaction equation

HRID 711278 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][NH:3]1.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1.CC1(C)N([O])C(C)(C)CCC1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[F:12][C:13]1[CH:18]=[C:17]([N:3]2[CH:4]=[CH:5][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:2]2=[O:1])[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylateHCID 2724126TempoHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 68083398HCID 68083398, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-oxo-1,2-dihydropyridine-4-carboxylate 89-1 (153 mg, 1.00 mmol), (3-fluorophenyl)boronic acid 6-6 (280 mg, 2.00 mmol), Cu(OAc)2 (36 mg, 0.2 mmol), molecular sieves (4 Å, activated, 200 mg), pyridine (162 μL, 2.0 mmol) and TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy, free radical, 172 mg, 1.1 mmol) in DCM (2.0 mL) was stirred at room temperature under dry air. The mixture was then filtered through celite (washed with ethyl acetate); and the filtrate was washed with 5% ammonia solution, dried with Na2SO4 and concentrated with rotavap. The residue was subjected to silica gel column chromatography with 1:3 ethyl acetate/DCM as eluent to give methyl 1-(3-fluorophenyl)-2-oxo-1,2-dihydropyridine-4-carboxylate as a solid 89-2.

Workup

  1. customunder dry air
  2. filtrationThe mixture was then filtered through celite (washed with ethyl acetate)
  3. washand the filtrate was washed with 5% ammonia solution
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated with rotavap

Sources & evidence

ORD record
ord-b204a2d48ea04527baac0932c7afd596
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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