Tetrahydrofuran → HCID 54186034, compound

HRID 1379538Notes

Reaction equation

HRID 1379538 reaction equation
O.Br[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[O:13].[C:14](=[O:17])([O-])[O-].[Na+].[Na+].[CH2:20]1[CH2:24]O[CH2:22][CH2:21]1>C(OCC)(=O)C>[CH3:9][N:8]1[C@H:7]2[C@@:20]([CH3:24])([C:20]3[CH:24]=[CH:4][C:3]([C:3]4[CH:4]=[C:5]5[C:9](=[CH:10][CH:11]=4)[NH:8][C:7](=[O:12])[C:6]5=[O:13])=[CH:11][C:21]=3[CH2:22][CH2:6]2)[CH2:21][CH2:22][C:14]1=[O:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 22125410HCID 22125410, compound

Product 1

HCID 54186034HCID 54186034, compoundYield 15%

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-bromoisatin hydrate (159 mg, 0.65 mmol), 0.65 mL of 2M 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 (5% methanol/ethyl acetate eluent) to give 36 mg (15%) of the title compound as a white solid. mp >250° FDMS: m/e=374. α[D]589 =+75.33 (c=0.53, 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 (5% methanol/ethyl acetate eluent)

Sources & evidence

ORD record
ord-efcc8832ca5242cc98f62de869a0f288
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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