Potassium Carbonate → 2-Methylamino-5-phenyl-nicotinic acid ethyl ester

HRID 2244355Notes

Reaction equation

HRID 2244355 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9](Br)[CH:8]=[N:7][C:6]=1[NH:12][CH3:13])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O1CCOCC1>O>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:8]=[N:7][C:6]=1[NH:12][CH3:13])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 687024045-Bromo-2-methylamino-nicotinic acid ethyl ester

Product 1

HCID 686955332-Methylamino-5-phenyl-nicotinic acid ethyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-bromo-2-methylamino-nicotinic acid ethyl ester (100 mg, 0.39 mmol), potassium carbonate (160 mg, 1.16 mmol), dichloro[1,1′-bis(diphenylphosphine)ferrocene]palladium(II); (28 mg, 39 μmol) and phenylboronic acid (146 mg, 1.16 mmol), 1,4-dioxane (0.9 mL), and water (0.11 mL) was heated at reflux for 3 h, then partitioned between ethyl acetate and sat. aq. ammonium chloride solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (44 mg, 44%). Yellow liquid, MS (EI): 256.2 (M+).

Workup

  1. temperatureat reflux for 3 h
  2. custompartitioned between ethyl acetate and sat. aq. ammonium chloride solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-61e84733db494117b8dfb8443e90078e
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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