Potassium Carbonate → 5,6-Dihydro-benzo[f]quinoline

HRID 520990Notes

Reaction equation

HRID 520990 reaction equation
Br[C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].F[B-](F)(F)F.C1([PH+](C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C(=O)C>[CH:7]1[C:2]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][CH2:8][C:3]=2[N:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11710396Tricyclohexylphosphonium TetrafluoroborateHCID 582943973-Bromo-2-phenethyl-pyridine

Product 1

HCID 158731845,6-Dihydro-benzo[f]quinoline

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

N,N-Dimethylacetamide (15 mL) is added to a flask charged with a stir bar, 3-bromo-2-phenethyl-pyridine (3.34 g), freshly dried K2CO3 (3.52 g), palladium(II) acetate (0.14 g), and tricyclohexylphosphonium tetrafluoroborate (0.47 g) and kept under argon atmosphere at room temperature. The flask is put into a 150° C. hot oil bath and the mixture is stirred therein for 2 h. After cooling the mixture to room temperature, the solvent is evaporated and the residue is chromatographed twice on silica gel (1. dichloromethane/methanol 98:2; 2. cyclohexane/ethyl acetate 90:10→50:50) to afford the title compound as an oil. Yield: 1.51 g (65% of theory); LC (method 1): tR=1.83 min; Mass spectrum (ESI+): m/z=182 [m+H]+.

Workup

  1. additioncharged with a stir bar
  2. customkept under argon atmosphere at room temperature
  3. customis put into a 150° C.
  4. customthe solvent is evaporated
  5. customthe residue is chromatographed twice on silica gel (1. dichloromethane/methanol 98:2; 2. cyclohexane/ethyl acetate 90:10→50:50)

Sources & evidence

ORD record
ord-6c85c3f435c94d85b5a77a43e4e446dc
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

Loading…