Potassium Acetate → HCID 23152423, compound

HRID 1012293Notes

Reaction equation

HRID 1012293 reaction equation
[CH2:1]([O:8][C:9]1[CH:37]=[CH:36][CH:35]=[CH:34][C:10]=1[O:11][CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=2)[C:16]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[C:15]1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[K+]>CN(C)C(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[C:10]2[O:11][CH2:12][CH2:13][N:14]3[C:15](=[C:16]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:17]4[CH:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:22]=43)[C:34]=2[CH:35]=[CH:36][CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 23152319HCID 23152319, compound

Product 1

HCID 23152423HCID 23152423, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of methyl 1-[2-(2-benzyloxyphenoxy)ethyl]-2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (2.61 g) in N,N-dimethylacetamide (100 ml) were added potassium acetate (905 mg, 9.22 mmol) and tetrakis(triphenylphosphine)palladium (800 mg, 0.69 mmol), and the mixture was stirred at 130° C. for 41 hr. The mixture was allowed to cool to room temperature, and filtered through celite. Saturated aqueous ammonium chloride solution was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous ammonium chloride solution and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=6:1) to give methyl 4-benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (745 mg, yield 34%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through celite
  3. additionSaturated aqueous ammonium chloride solution was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with saturated aqueous ammonium chloride solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-b7e2b02e045749128875a57ea739e45d
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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