Sodium Carbonate → HCID 57475134, compound

HRID 1095507Notes

Reaction equation

HRID 1095507 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][Si:10]([CH3:17])([CH3:16])[C:11]#[C:12][CH2:13][CH2:14][CH3:15].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)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.C(Cl)Cl>[CH2:13]([C:12]1[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:4][C:11]=1[Si:10]([CH3:17])([CH3:16])[CH3:9])[CH2:14][CH3:15]

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 119952-IodoanilineHCID 433294Lithium ChlorideHCID 27608601-(Trimethylsilyl)-1-pentyne

Product 1

HCID 57475134HCID 57475134, compoundYield 50%

Reagents, catalysts & solvents 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
108.5 °C

Procedure

2-Iodoaniline (4.65 g, 21.2 mmol), trimethyl(pent-1-ynyl)silane (3.27 g, 23.3 mmol), lithium chloride (0.96 g, 22.6 mmol) and sodium carbonate (6.75 g, 63.7 mmol) were combined in dimethylformamide (absolute, 64 ml) in an argon atmosphere. The catalyst ([Pd(dppf)Cl2×CH2Cl2], 1.78 g, 2.2 mmol) was then added. The solution was stirred at 105-112° C. (oil bath temperature) for 7 h. The black reaction mixture was cooled to room temperature and water (200 ml) and ethyl acetate (200 ml) were added in succession. After stirring for one hour, the mixture was filtered over Celite. The phases were separated. The organic phase was washed with 10 per cent strength citric acid solution (100 ml) and with saturated sodium chloride solution (100 ml). The organic phase was dried with sodium sulfate. After filtration, the volatile constituents were removed completely in vacuo. The residue (7.03 g of brown oil) was separated by chromatography [silica gel 60 (150 g); cyclohexane/trichloromethane 10:1 (550 ml); cyclohexane/trichloromethane 5:1 (1,650 ml)]. 2.35 g (50%) of 3-propyl-2-trimethylsilanyl-1H-indole were isolated as a brown oil (contaminated).

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. washThe organic phase was washed with 10 per cent strength citric acid solution (100 ml) and with saturated sodium chloride solution (100 ml)
  7. dry with materialThe organic phase was dried with sodium sulfate
  8. filtrationAfter filtration
  9. customthe volatile constituents were removed completely in vacuo
  10. customThe residue (7.03 g of brown oil) was separated by chromatography [silica gel 60 (150 g); cyclohexane/trichloromethane 10:1 (550 ml); cyclohexane/trichloromethane 5:1 (1,650 ml)]

Sources & evidence

ORD record
ord-eb616b3c1c294d918f9f1a11273eca3d
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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