Tetrahydrofuran → HCID 53797615, compound

HRID 1780489Notes

Reaction equation

HRID 1780489 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:12](=[O:15])([O-])[O-].[Na+].[Na+].[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>C(Cl)(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:5][N:4]1[C@H:3]2[C@@:18]([CH3:22])([C:18]3[CH:22]=[CH:8][C:7]([C:2]4[CH:3]=[N:4][C:5]5[C:10]([CH:11]=4)=[CH:9][CH:8]=[CH:7][CH:6]=5)=[CH:6][C:19]=3[CH2:20][CH2:2]2)[CH2:19][CH2:20][C:12]1=[O:15]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 214133-Bromoquinoline

Product 1

HCID 53797615HCID 53797615, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6212ChloroformSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid (178 mg, 0.65 mmol), tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.02 mmol), 3-bromoquinoline (135 mg, 0.65 mmol), 0.65 mL of 2M sodium carbonate solution and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. An additional 23 mg of the palladium reagent was added, and the mixture was heated an additional 24 h. The mixture was cooled, diluted with chloroform (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent) to give 130 mg (56%) of the title compound as an amorphous solid. mp: 180°-185°. FDMS: m/e=356. α[D]589 =+80.22 (c=0.37,chloroform).

Workup

  1. customfitted with a reflux condenser
  2. temperaturethe stirred mixture was heated at 80°, under nitrogen, for 24 h
  3. temperaturethe mixture was heated an additional 24 h
  4. temperatureThe mixture was cooled
  5. washwashed with brine (2×25 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (ethyl acetate eluent)

Sources & evidence

ORD record
ord-37dd9d93fc9f47ae98912c86476e2852
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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