3-Butyn-2-ol → 4-Methoxy-7-(3-hydroxy-1-butyn-1-yl)-6-azaindole

Participants

Role	Name	HCID	Charge
Reactant	3-Butyn-2-ol	HCID 16239	—
Reactant	Tris(furan-2-yl)phosphane	HCID 521585	—
Reactant	7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridine	HCID 20791244	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(benzonitrile)palladium chloride	HCID 498840	—
Solvent	Piperidine	HCID 8082	—
Product	4-Methoxy-7-(3-hydroxy-1-butyn-1-yl)-6-azaindole	HCID 59681670	105.1%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a mixture of 4-methoxy-7-bromo-6-azaindole (0.200 g, 0.88 mmol), PdCl2(PhCN)2 (0.017 g, 0.044 mmol), tri-2-furylphosphine (0.0410 g, 0.176 mmol) and CuI (0.017 g, 0.088 mmol) was added piperidine (10 mL), followed by 3-butyn-2-ol (0.09 mL, 1.15 mmol). The mixture was heated at 80° C. for 6 h and then the solvent was removed in vacuo. The residue was partitioned with EtOAc-H2O and then the aqueous phase was separated and re-extracted with EtOAc (×2). The combined organic layers were washed (H2O, brine), dried (Na2SO4) and concentrated to afford the title compound (0.200 g, 95%) as a brown solid which was of sufficient purity for use in the following step:

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915283B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-6704980383aa4cfa8c74e64ce0912a8e
Source note	uspto-grants-2011_03