Sodium Carbonate → 3-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

HRID 58635Notes

Reaction equation

HRID 58635 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1I.[CH2:11]([Si:13]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:14]#[C:15][CH2:16][CH2:17][OH:18])[CH3:12].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[OH:18][CH2:17][CH2:16][C:15]1[C:3]2[C:2](=[CH:9][CH:8]=[C:5]([C:6]#[N:7])[CH:4]=2)[NH:1][C:14]=1[Si:13]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:11][CH3:12]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 44163954-Amino-3-iodobenzonitrile

Product 1

HCID 668321333-(2-hydroxyethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrileYield 51.8%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Procedure

4-amino-3-iodobenzonitrile (1.65 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (1.57 mL; 7.44 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.276 g; 0.338 mmol), lithium chloride (0.287 g; 6.76 mmol), sodium carbonate (1.43 g; 13.52 mmol) in DMF (14 mL) was stirred at 100° C. for 15 hours. The solution was filtered through celite, diluted in ethyl acetate, washed with brine and sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane) to yield 0.873 g (43%) of the title compound as a yellow solid.

Workup

  1. filtrationThe solution was filtered through celite
  2. additiondiluted in ethyl acetate
  3. washwashed with brine and sodium thiosulphate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified by flash chromatography on silica (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-852fc4767c60491383d952da2fa0d845
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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