Tetrahydrofuran → HCID 53646547, compound

HRID 1379541Notes

Reaction equation

HRID 1379541 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:14](=[O:17])([O-])[O-].[Na+].[Na+].[CH2:20]1[CH2:24]O[CH2:22][CH2:21]1>C(Cl)(Cl)Cl>[CH3:5][N:4]1[C@H:1]2[C@@:20]([CH3:24])([C:20]3[CH:24]=[CH:8][C:7]([C:9]4[CH:8]=[C:7]5[C:12](=[CH:11][CH:10]=4)[N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]5)=[CH:6][C:21]=3[CH2:22][CH2:2]2)[CH2:21][CH2:22][C:14]1=[O:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 7218471-(5-bromo-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 53646547HCID 53646547, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 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), 1-acetyl-5-bromoindoline (156 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 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 (5% methanol/ethyl acetate eluent) to give 67 mg (26%) of the title compound as a yellow solid. mp 197°-200°. FDMS: m/e=388. α[D]589 =+77.92 (c=0.36, 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-cc728de83210443287bddaff446c00cb
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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