Dimethylformamide → HCID 57475156, compound

HRID 1095551Notes

Reaction equation

HRID 1095551 reaction equation
[CH2:1]([Si:3]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:4]#[C:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl.C[N:29]([CH3:32])C=O>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].C(OCC)(=O)C.O>[CH2:6]([C:5]1[C:8]2[C:32](=[CH:4][CH:5]=[CH:6][CH:7]=2)[NH:29][C:4]=1[Si:3]([CH2:1][CH3:2])([CH2:13][CH3:14])[CH2:15][CH3:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 66783162HCID 66783162, compound

Product 1

HCID 57475156HCID 57475156, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
103 °C

Procedure

3-Benzyl-2-triethylsilanyl-1H-indole2-Iodoaniline (5.48 g, 25.02 mmol), triethyl-(3-phenylprop-1-ynyl)silane (6.34 g, 27.51 mmol), lithium chloride (1.11 g, 26.19 mmol) and sodium carbonate (7.95 g, 75.01 mmol) were combined in dimethylformamide (absolute, 70 ml) in an argon atmosphere. The catalyst ([Pd(dppf)Cl2×CH2Cl2], 2.05 g, 2.51 mmol) was then added. The solution was stirred at 100-106° C. for 6 h. The black reaction mixture was cooled to room temperature and water (300 ml) and ethyl acetate (150 ml) were added in succession. After stirring for one hour, the mixture was filtered over Celite. The phases were separated. The aqueous phase was extracted with ethyl acetate (3×50 ml). The combined organic phases were dried with sodium sulfate. After filtration, the volatile constituents were removed completely in vacuo. The residue (10.5 g of brown oil) was purified by chromatography [silica gel 60 (300 g); cyclohexane/ethyl acetate 10:1 (2,200 ml)]. 3-Benzyl-2-triethylsilanyl-1H-indole was isolated as a brown oil (6.44 g, (80%).

Workup

  1. customThe black reaction mixture
  2. temperaturewas cooled to room temperature
  3. stirringAfter stirring for one hour
  4. filtrationthe mixture was filtered over Celite
  5. customThe phases were separated
  6. extractionThe aqueous phase was extracted with ethyl acetate (3×50 ml)
  7. dry with materialThe combined organic phases were dried with sodium sulfate
  8. filtrationAfter filtration
  9. customthe volatile constituents were removed completely in vacuo
  10. customThe residue (10.5 g of brown oil) was purified by chromatography [silica gel 60 (300 g); cyclohexane/ethyl acetate 10:1 (2,200 ml)]

Sources & evidence

ORD record
ord-cda26c92dded400b82d1c34b90683cfd
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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