Potassium Carbonate → Benzo[c][1,8]naphthyridin-6(5H)-one

HRID 1029069Notes

Reaction equation

HRID 1029069 reaction equation
[NH2:1][C:2]1[C:7](I)=[CH:6][C:5](Br)=[CH:4][N:3]=1.C[O:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O)=O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:6]1[CH:5]=[CH:4][N:3]=[C:2]2[C:7]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12](=[O:11])[NH:1]2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 15165082-Amino-5-bromo-3-iodopyridineHCID 27734962-(Methoxycarbonyl)benzeneboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 12342815Benzo[c][1,8]naphthyridin-6(5H)-oneYield 7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

2-Amino-3-iodo-5-bromopyridine (299 mg, 1.00 mmol), 2-methoxycarbonylphenylboronic acid (189 mg, 1.05 mmol), palladium(II) acetate (9 mg, 0.04 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (33 mg, 0.08 mmol), and potassium carbonate (414 mg, 3.00 mmol) were dissolved in dioxane/H2O (2.0 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, suspended in EtOAc/H2O, and filtered. The precipitate was washed with EtOAc/H2O, and dried under vacuum to provide 1 (6 mg, 7% yield) as a solid. LC-MS (M+H=275, obsd.=275). 1H NMR (400 MHz, d6-DMSO): δ 12.22 (s, 1H), 9.11 (d, 1H), 8.64 (d, 1H), 8.61 (d, 1H), 8.33 (d, 1H), 7.91 (t, 1H), 7.73 (t, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. washThe precipitate was washed with EtOAc/H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b090bc9bdb7a4153aa8546293de549e4
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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