Tetrahydrofuran → HCID 53789570, compound

HRID 1780491Notes

Reaction equation

HRID 1780491 reaction equation
[S:1]([N:11]1[C:19]2[C:14](=[CH:15][C:16](Br)=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:21](=[O:24])([O-])[O-].[Na+].[Na+].[CH2:27]1[CH2:31]O[CH2:29][CH2:28]1>C(OCC)(=O)C.[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>[CH3:19][N:11]1[C@H:12]2[C@@:27]([CH3:31])([C:27]3[CH:31]=[CH:10][C:4]([C:16]4[CH:15]=[C:14]5[C:19](=[CH:18][CH:17]=4)[N:11]([S:1]([C:4]4[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=4)(=[O:3])=[O:2])[CH:12]=[CH:13]5)=[CH:5][C:28]=3[CH2:29][CH2:13]2)[CH2:28][CH2:29][C:21]1=[O:24]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 119546185-Bromo-1-(4-methylbenzene-1-sulfonyl)-1H-indole

Product 1

HCID 53789570HCID 53789570, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 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), N-tosyl-5-bromoindole (228 mg, 0.65 mmol),0.65 mL of 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 49 mg (15%) of the title compound as an amorphous foam. FDMS: m/e=498.

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-b53f1c8dd92748d294253d1b3184f2d2
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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