Water → Indole

HRID 1095505Notes

Reaction equation

HRID 1095505 reaction equation
C(Cl)Cl.O.C[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12](C(F)(F)F)[CH:13]=2)[NH:8][C:7]=1[Si](C)(C)C.CC1NC2C(C=1[Si](C)(C)C)=CC(C(F)(F)F)=CC=2>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C.C(OCC)(=O)C>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

8

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 57475130HCID 57475130, compoundHCID 57475131HCID 57475131, compound

Product 1

HCID 798Indole

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

[Pd(dppf)Cl2×CH2Cl2]; 327 mg, 0.4 mmol) was then added. The reaction mixture was stirred at 100° C. (oil bath temperature) for 6 h and at room temperature for 18 h. The reaction mixture was then cooled with ice water, water (50 ml) and ethyl acetate (100 ml) were added and the mixture was stirred for 30 min. In order to separate off the catalyst, the dark brown mixture was filtered over Celite. The phases of the filtrate were separated. The aqueous phase was extracted with ethyl acetate (5×35 ml). The combined organic phases were washed with saturated sodium chloride solution (3×35 ml), subsequently dried with sodium sulfate, filtered and concentrated in vacuo. The dark brown oil obtained (1.8 g) which, apart from 3-methyl-5-trifluoromethyl-2-trimethylsilanyl-1H-indole, contained traces of DMF and also the isomer 2-methyl-5-trifluoromethyl-3-trimethylsilanyl-1H-indole, was employed as the crude product for the next stage.

Workup

  1. addition327 mg, 0.4 mmol) was then added
  2. waitat room temperature for 18 h
  3. additionwere added
  4. stirringthe mixture was stirred for 30 min
  5. customIn order to separate off the catalyst
  6. filtrationthe dark brown mixture was filtered over Celite
  7. customThe phases of the filtrate were separated
  8. extractionThe aqueous phase was extracted with ethyl acetate (5×35 ml)
  9. washThe combined organic phases were washed with saturated sodium chloride solution (3×35 ml)
  10. dry with materialsubsequently dried with sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe dark brown oil obtained (1.8 g) which

Sources & evidence

ORD record
ord-971bb073fd594111ac3d5cccd8dc5c57
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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