Hydrochloric Acid → HCID 23152661, compound

HRID 1012354Notes

Reaction equation

HRID 1012354 reaction equation
Br[C:2]1[N:3]([CH2:21][S:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.C([O-])(=O)C.[K+].Cl>CN(C)C(=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>[CH:11]1([C:10]2[C:9]3[C:4]([N:3]4[C:2]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[S:22][CH2:21]4)=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 23152275HCID 23152275, compound

Product 1

HCID 23152661HCID 23152661, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of methyl 2-bromo-3-cyclohexyl-1-phenylsulfanylmethyl-1H-indole-6-carboxylate (1.10 g, 2.41 mmol), potassium acetate (260 mg, 2.64 mmol) and tetrakis(triphenylphosphine) palladium (279 mg, 0.24 mmol) in N,N-dimethylacetamide (30 ml) was stirred at 100° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, 2N hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=20:1-7:1) to give methyl 11-cyclohexyl-5-thia-6a-azabenzo[a]fluorene-8-carboxylate (100 mg, yield 11.0%).

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was successively washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=20:1-7:1)

Sources & evidence

ORD record
ord-b833be91d776485e8cd40e555e0dbd7b
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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