Sodium Thiosulfate → HCID 90409204, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Thiosulfate	HCID 24477	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate	HCID 4642098	—
Reactant	4-Bromo-2-iodo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine	HCID 37818650	—
Catalyst	Tetrakis(triphenylphosphine)palladium	HCID 11979704	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 90409204	HCID 90409204	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a suspension of Example 5B (20 g, 41.9 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (16.85 g, 54.5 mmol), and tetrakis(triphenylphosphine)palladium(O) (4.84 g, 4.19 mmol) in N,N-dimethylformamide (500 mL) was added a solution of sodium bicarbonate (7.04 g, 84 mmol) in water (40 mL) and the mixture was stirred at 80° C. for 12 hours. Saturated aqueous sodium thiosulfate, water and ethyl acetate were added and the aqueous layer was extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrated to provide the title compound. MS (CI) m/z 532 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09328112B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-3b737e665eff4ae8a302aafa944a5c97
Source note	uspto-grants-2016_05