Tris(1,1-dimethylethyl)phosphine → HCID 66679380, compound

Participants

Role	Name	HCID	Charge
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	Potassium Fluoride	HCID 522689	—
Reactant	Benzo[b]furan-2-boronic acid	HCID 2776266	—
Reactant	4-Chloro-1H-pyrrolo[2,3-b]pyridine	HCID 11389493	—
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	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 66679380	HCID 66679380	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

4-Chloro-7-azaindole (119, 100 mg, 0.66 mmol, prepared as described in Example 70, Scheme 81), 2-Benzofuranboronic acid (212 mg, 1.31 mmol) and Potassium fluoride (127 mg, 2.18 mmol) were stirred in 3 mL of anhydrous dioxane. Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (10.2 mg, 9.83E-3 mmol) and tri t-butylphosphine (6.6 mg, 0.033 mol) were added and the suspension was stirred at 100° C. for 4 hours in a pressure tube under inert atmosphere. The reaction mixture was cooled to room temperature and was adsorbed onto silica gel and purified by chromatography to provide the compound (120, 56 mg, 36%). MS (ESI) [M+H+]+=235.20.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08470818B2
Source dataset	uspto-grants-2013_06
ORD ID	ord-f856a25b302b430c88f6780c98e15224
Source note	uspto-grants-2013_06