Sodium Carbonate → HCID 46236050, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	tert-Butyl 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl)piperazine-1-carboxylate	HCID 53216820	—
Reactant	5-bromo-3-(1H-indol-5-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 66779176	—
Solvent	Acetonitrile	HCID 6342	—
Product	HCID 46236050	HCID 46236050	35.1%

Reaction Conditions

Temperature	150 °C

Reaction Steps

Intermediate B (131 mg) and tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperazine-1-carboxylate (136 mg) were suspended in 2 mL of acetonitrile and treated with 2 mL of 1 M sodium carbonate solution and dichloro-bis-(triphenylphosphine)-palladium(II) (10 mg). The resulting mixture was heated in a microwave reactor cell for 20 minutes at 150° C., resulting in de-tosylated material which was purified by MPLC chromatography (0-3% methanol) to provide an analytical sample of the title compound (50 mg, 508 M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846909B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-24db11e5b65d41f59a52f56ecaa2e73a
Source note	uspto-grants-2014_09