Tetrahydrofuran → HCID 54559988, compound

HRID 1379537Notes

Reaction equation

HRID 1379537 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])=[N:6][CH:7]=1.[C:15](=[O:18])([O-])[O-].[Na+].[Na+].[CH2:21]1[CH2:25]O[CH2:23][CH2:22]1>C(OCC)(=O)C>[CH3:7][N:6]1[C@H:5]2[C@@:21]([CH3:25])([C:21]3[CH:25]=[CH:12][C:11]([C:2]4[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])=[N:6][CH:7]=4)=[CH:9][C:22]=3[CH2:23][CH2:4]2)[CH2:22][CH2:23][C:15]1=[O:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 15461537N-(5-bromopyridin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 54559988HCID 54559988, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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), 5-bromo-2-(t-butylcarbonylamino)pyridine (167 mg, 0.65 mmol), 0.65 mL of 2M aqueous sodium carbonate and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. The mixture was cooled, diluted with ethyl acetate (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 84 mg (32%) of the title compound as a brown solid. mp 248°-250°. FDMS: m/e=405. α[D]589 =+70.74 (c=0.45, 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 cooled
  4. washwashed with brine (2×25 mL)
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (ethyl acetate eluent)

Sources & evidence

ORD record
ord-6a5fdd0876b84f52acaec769c84efd6c
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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