Potassium Carbonate → 6-(Pyridin-3-yl)-3,4-dihydroquinolin-2(1H)-one

HRID 1521570Notes

Reaction equation

HRID 1521570 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]3)[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 137288626-(Pyridin-3-yl)-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)Catalyst

Conditions

Temperature
100 °C

Procedure

A sealable tube containing 6-bromo-3,4-dihydroquinolin-2(1H)-one (0.10 g, 0.44 mmol), 3-pyridylboronic acid (0.56 g, 4.6 mmol), bis(di-tert-butyl(4-dimethylamino phenyl)phosphine)dichloropalladium(II) (6.3 mg, 8.9 μmol), and potassium carbonate (0.18 g, 1.3 mmol) was flushed with nitrogen before tert-butanol (4.9 mL) and water (0.6 mL) were added. The tube was flushed again with nitrogen, sealed tightly and heated to 100° C. overnight. The reaction was then cooled to room temperature, poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic extracts were combined, washed with water, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-15% methanol in ethyl acetate) provided the title compound: LCMS m/z 225.27 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.77 (s, 1H), 8.47 (d, J=4.8 Hz, 1H), 8.06 (ddd, J=1.7, 2.0, 8.1 Hz, 1H), 7.52 (s, 1H), 7.50-7.47 (m, 2H), 6.99 (d, J=8.1 Hz, 1H), 3.05 (t, J=7.5, 7.7 Hz, 2H), 2.61 (t, J=7.5, 7.7 Hz, 2H).

Workup

  1. customwas flushed with nitrogen before tert-butanol (4.9 mL) and water (0.6 mL)
  2. additionwere added
  3. customThe tube was flushed again with nitrogen
  4. customsealed tightly
  5. temperatureThe reaction was then cooled to room temperature
  6. additionpoured into saturated aqueous sodium chloride solution
  7. extractionextracted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by flash chromatography on silica gel (0-15% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-00b6d255d4d34dcebfd2a05cf70c9c60
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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