Water → HCID 59212606, compound

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	HCID 59212611	HCID 59212611	—
Catalyst	Zinc cyanide (Zn(CN)2)	HCID 11186	—
Catalyst	Zinc Acetate	HCID 11192	—
Catalyst	Zinc	HCID 23994	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Product	HCID 59212606	HCID 59212606	43%

Reaction Steps

The title compound of Example 13.1 (4.97 g, 12.61 mmol), dppf (0.042 g, 0.076 mmol), zinc cyanide (0.89, 7.57 mmol), Pd2(dba)3 (0.026 g, 0.025 mmol), zinc acetate (0.185 g, 1.01 mmol) and Zn dust (0.066 g, 1.01 mmol) were stirred in DMF (50 mL) and water (1.5 mL) for 12 h at 90° C. and a further 6 h at 120° C. The reaction mixture was partitioned between ethyl acetate and water. The organic extracts were dried over sodium sulphate, filtered and concentrated and purified by column chromatography to afford the title product (1.83 g, 43%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07678796B2
Source dataset	uspto-grants-2010_03
ORD ID	ord-ce2adbe8f870468d9c9ff225beb07535
Source note	uspto-grants-2010_03