Tetrahydrofuran → 3-Morpholin-4-yl-1-triisopropylsilanyl-1H-indole

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Morpholine	HCID 8083	—
Reactant	Lithium Hexamethyldisilazide	HCID 2733832	—
Reactant	3-Bromo-1-(triisopropylsilyl)indole	HCID 10991769	—
Catalyst	2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl	HCID 2734217	—
Catalyst	Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)	HCID 11029508	—
Product	3-Morpholin-4-yl-1-triisopropylsilanyl-1H-indole	HCID 58975176	60%

Reaction Conditions

Temperature	65 °C

Reaction Steps

Combine 3-bromo-1-triisopropylsilanyl-1H-indole (0.33 g, 0.94 mmol), morpholine (0.10 mL, 1.15 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.012 g, 0.03 mmol), and tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.012 g, 0.01 mmol) in a pressure tube. Add 1N solution of lithium bis(trimethylsilyl)amide in THF (2.00 mL, 2.00 mmol), flush tube with nitrogen gas, and close the tube. Stir at 65° C. for 18 h, cool to room temperature, dilute with water, and extract with EtOAc. Wash EtOAc layer with water, brine, dry (Na2SO4), and concentrate under vacuum. Purify the residue by flash chromatography using 0 to 50% of EtOAc in hexanes to give the title compound (0.20 g 60%): MS (ES) 359.1 (M+1)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07595339B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-39272f2a039c4af58642dca180712093
Source note	uspto-grants-2009_09