Potassium Phosphate, Tribasic → 3-Cyclopropyl-1-triisopropylsilanyl-1H-indole

HRID 736979Notes

Reaction equation

HRID 736979 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.[CH:21]1(B(O)O)[CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:21]1([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=2)[CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 109917693-Bromo-1-(triisopropylsilyl)indole

Product 1

HCID 589750793-Cyclopropyl-1-triisopropylsilanyl-1H-indoleYield 84.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Dissolve 3-bromo-1-triisopropylsilanyl-1H-indole (1.02 g, 2.89 mmol), cyclopropylboronic acid (259 mg, 3.01 mmol) and K3PO4 (1.8 g, 8.5 mmol) in a mixture of toluene (20 mL) and water (0.8 mL). Add tricyclohexyl-phosphane (86 mg, 0.31 mmol) and palladium(II) acetate (50 mg, 0.22 mmol) and stir the mixture at 70° C. for 3 h. Filter the mixture through celite and wash the solids with EtOAc (30 mL). Collect and concentrate the filtrate and purify the residue by flash chromatography, using a linear gradient of 100% hexanes to 10% EtOAc/hexanes, to give the title compound as a clear oil 765 mg (84%): MS (ES) 314.1 (M+1)+.

Workup

  1. filtrationFilter the mixture through celite
  2. washwash the solids with EtOAc (30 mL)
  3. customCollect
  4. concentrationconcentrate the filtrate
  5. custompurify the residue by flash chromatography

Sources & evidence

ORD record
ord-9e50daf8216845928819f6adb17e16a4
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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