Dichloromethane → HCID 86727396, compound

https://huagongshe.com/reaction/519034

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane	HCID 10997426	—
Reactant	HCID 86727397	HCID 86727397	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 86727396	HCID 86727396	75%

Reaction Steps

A mixture of 3-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.080 g, 0.166 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.084 g, 0.499 mmol), K2CO3 (0.046 g, 0.332 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.014 g, 0.017 mmol) in dioxane (3 mL) and H2O (0.5 mL) was stirred at 90° C. for 15 h. The solvent was removed in vacuo and the residue was purified by preparative TLC (eluting with 30% EtOAc in petroleum ether) to give 3-(7-isopropenyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester as a white solid (0.055 g, 75%). LC/MS (Table 1, Method 2) Rt=1.240 min.; MS m/z: 443 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115151B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-6b85e694bec14aea8fb5ec9ff0021ed0
Source note	uspto-grants-2015_08