Dimethylamine → 3-Dimethylamino-1-fluoro-7-bromo-10-Boc-phenothiazine

Participants

Role	Name	HCID	Charge
Reactant	Dimethylamine	HCID 674	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	3,7-Dibromo-1-fluoro-10-Boc-phenothiazine	HCID 68227324	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Toluene	HCID 1140	—
Product	3-Dimethylamino-1-fluoro-7-bromo-10-Boc-phenothiazine	HCID 68227340	—

Reaction Steps

To a stirred solution of 3,7-dibromo-1-fluoro-10-Boc-phenothiazine (1.43 g, 3.0 mmol) in toluene (60 mL) in 75 mL pressure vessel Pd(dba)2 (86.3 mg, 0.15 mmol), BINAP (67.3 mg, 0.11 mmol), Cs2CO3 (978 mg, 3.0 mmol) and dimethylamine (1.5 mL, 2 M solution in THF) were added. The mixture was refluxed for 24 h. After that reaction mixture was filtered, solvent was removed under vacuum. Product was used without additional purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08828986B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-7213fd8dcaf94606967e30e89c487aca
Source note	uspto-grants-2014_09