Ethyl Acetate → US10023592, Example 365

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	2-[2-(Cyclopropylmethoxy)-5-(ethylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 89657518	—
Reactant	8-bromo-6-methyl-4,6-dihydro-2H-pyrido[4,3-b][1,4]oxazine-3,5-dione	HCID 118021431	—
Solvent	Hexane	HCID 8058	—
Product	US10023592, Example 365	HCID 118023002	—

Reaction Steps

The title compound of step 2 was reacted with 2-[2-(cyclopropylmethoxy)-5-ethylsulfonylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in a manner similar to Example 224, step 5. Silica gel chromatography (40-100% EA in hexane over 8 min) gave the title compound. 1H NMR: (DMSO-d6, 400 MHz) δ ppm 0.27-0.33 (m, 2H) 0.51-0.57 (m, 2H) 1.11 (t, J=7.33 Hz, 3H) 1.14-1.22 (m, 1H, partially obscured) 3.22-3.28 (m, 2H) 3.51 (s, 3H) 3.96 (d, J=7.07 Hz, 2H) 4.54 (s, 2H) 7.27 (d, J=8.84 Hz, 1H) 7.52 (s, 1H) 7.67 (d, J=2.02 Hz, 1H) 7.79-7.92 (m, 1H) 10.10 (s, 1H) LCMS: 419 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034900B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-6072af5c6d5e463f92ebb37788cb71ab
Source note	uspto-grants-2015_05