Cyclopropanecarbonyl chloride → US10023592, Example 220

Participants

Role	Name	HCID	Charge
Reactant	Cyclopropanecarbonyl chloride	HCID 77637	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Bromo-4-methanesulfonylaniline	HCID 20134402	—
Reactant	2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one	HCID 123809499	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	US10023592, Example 220	HCID 118021459	—

Reaction Steps

2-bromo-4-methanesulfonylaniline was coupled to the title compound of Example 89, step 1 in a manner similar to Example 89, step 2. The resulting product was reacted with cyclopropanecarbonyl chloride using diisopropylethylamine in THF to prepare the title compound. 1H NMR (CDCl3, 400 MHz) δ 9.38 (s, 1H), 8.34 (d, J=8.0 Hz, 1H), 8.23 (d, J=8.8 Hz, 1H), 7.96 (d, J=8.8 Hz, 1H), 7.83 (s, 1H), 7.53-7.64 (m, 3H), 6.94 (d, J=8.0 Hz, 1H), 3.59 (s, 3H), 3.25 (m, 3H), 1.64 (brs, 1H), 0.52-0.75 (m, 4H). LCMS: 397.0 (M+1)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115114B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-dec0ce06f51548c9b2189871d34667e9
Source note	uspto-grants-2015_08