Sodium Bicarbonate → HCID 90412055, compound

https://huagongshe.com/reaction/1521997

Participants

Role	Name	HCID	Charge
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-Chloro-5-fluoro-2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine	HCID 90413904	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Sodium chloride dihydrate	HCID 23713072	—
Product	HCID 90412055	HCID 90412055	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of Example 231B (6.70 g, 15.34 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (4.89 g, 15.81 mmol), tetrakis(triphenylphosphine)palladium (0.532 g, 0.460 mmol), and sodium bicarbonate solution (40 mL, 15.34 mmol) in N,N-dimethylformamide (160 mL) was degassed and heated at 80° C. overnight. The mixture was diluted with water/brine and extracted with ethyl acetate (twice). The combined organic layers were washed with water, dried over magnesium sulfate, filtered, concentrated, and purified on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (8:2 to 7:3) to give the title compound. MS (ESI+) m/z 492.0 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09073922B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-783e8ec877474ea7a8caf65c5ef5d1ef
Source note	uspto-grants-2015_07