Potassium Carbonate → HCID 86712875, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Bromo-3-methylpyridine	HCID 220832	—
Reactant	8-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-{1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine	HCID 86712860	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	HCID 86712875	HCID 86712875	83%

Reaction Steps

A solution of the compound (555 mg, 1.0 mmol) obtained in Example 16-5), 2-bromo-3-picoline (344 mg, 2 mmol), tetrakis(triphenylphosphine)palladium(0) (231 mg, 0.2 mmol), and potassium carbonate (276 mg, 2 mmol) in dimethoxyethane (4 mL) and water (1 mL) was stirred at 100° C. for 1 h under microwave irradiation. The reaction mixture was cooled to room temperature and purified by silica gel chromatography (Isco Combiflash, 40 g, methanol:ethyl acetate=0:100 to 20:80, gradient) to obtain the title compound (430 mg, 83%) as a light yellow oily substance.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08927536B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-761caac3b0c24034a287678a61f6aea8
Source note	uspto-grants-2015_01