Water → 2-Methyl-6,7-dihydro-8H-indeno[5,4-d]thiazol-8-one

HRID 883196Notes

Reaction equation

HRID 883196 reaction equation
[NH2:1][C:2]1[C:10](I)=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:12])=[CH:4][CH:3]=1.[C:13](N)(=[S:15])[CH3:14].[O-2].[Ca+2].O>CN(C)C=O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:14][C:13]1[S:15][C:10]2[C:9]3[C:8](=[O:12])[CH2:7][CH2:6][C:5]=3[CH:4]=[CH:3][C:2]=2[N:1]=1

Participants

8

Reactant 4

HCID 962WaterHCID 2723949ThioacetamideHCID 6850728CalciumoxideHCID 577812296-amino-7-iodo-2,3-dihydro-1H-inden-1-one

Product 1

HCID 577812782-Methyl-6,7-dihydro-8H-indeno[5,4-d]thiazol-8-oneYield 46%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

6-Amino-7-iodoindan-1-one (1.00 g, 3.66 mmol), thioacetamide (413 mg, 5.49 mmol), 1,1′-bis(diphenylphosphino)ferrocene (383 mg, 1.46 mmol), calcium oxide (411 mg, 7.32 mmol) and tris(dibenzylideneacetone)dipalladium(0) (335 mg, 0.37 mmol) were dissolved in N,N-dimethylformamide (12 mL), and the mixture was stirred at 60° C. for 1 hr. After allowing to cool to room temperature, water was added to the reaction solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→65/35), and then purified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60) to give the title compound (340 mg, yield 46%).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→65/35)
  6. custompurified by silica gel column chromatography (NH, ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-0f09a593f08c41d1b791f99f5da32c6d
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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