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

HRID 1029068Notes

Reaction equation

HRID 1029068 reaction equation
[NH2:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][N:3]=1.C[O:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O)=O.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:6]1[CH:5]=[CH:4][N:3]=[C:2]2[C:7]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11](=[O:10])[NH:1]2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 8177002-Amino-3-bromopyridineHCID 27734962-(Methoxycarbonyl)benzeneboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 12342815Benzo[c][1,8]naphthyridin-6(5H)-oneYield 38.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

2-Amino-3-bromopyridine (173 mg, 1.00 mmol), 2-methoxycarbonyl-phenylboronic acid (225 mg, 1.25 mmol), Pd(OAc)2 (9 mg, 0.04 mmol), S-Phos (33 mg, 0.08 mmol), and K2CO3 (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 (75 mg, 38% yield) as a solid. LC-MS (M+H=197, obsd.=197). 1H NMR (400 MHz, d6-DMSO): δ 12.08 (s, 1H), 8.83 (d, 1H), 8.55 (d, 1H), 8.49 (dd, 1H), 8.42 (d, 1H), 7.90 (t, 1H), 7.70 (t, 1H), 7.33 (dd, 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-2cacda9ed96e45b38b4e33f99b03d014
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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