Potassium Phosphate, Tribasic → 5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one

HRID 1521664Notes

Reaction equation

HRID 1521664 reaction equation
Cl[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.[CH:13]1(B(O)O)[CH2:15][CH2:14]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:13]1([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH2:4][CH2:5][C:6](=[O:12])[NH:7]3)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 190277365-chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 891570455-cyclopropyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 5-chloro-3,4-dihydroquinolin-2(1H)-one (147-4; 1 g, 0.0055 mol) and cyclopropylboronic acid (0.95 g, 0.0110 mol) in tetrahydrofuran (30 mL) was added potassium phosphate (3.4 g, 0.0165 mol) and S-Phos (0.45 g, 0.0011 mol). Reaction mass was purged with argon for 20 min. Then catalyst palladium acetate (0.123 g, 0.00055 mol) was added and allowed to stir at 120° C. for 12 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic part was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography to obtain title compound. MS (M+1): 188.1.

Workup

  1. customReaction mass
  2. customwas purged with argon for 20 min
  3. filtrationThe reaction mixture was filtered through CELITE bed
  4. filtrationfilter bed
  5. washwas thoroughly washed with ethyl acetate
  6. concentrationThe collected organic part was concentrated under vacuum
  7. customto afford the crude compound, which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8fd4e810a2224416a6b56c4f73323882
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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