Iodoethane → US10023592, Example 216

Participants

Role	Name	HCID	Charge
Reactant	Iodoethane	HCID 6340	—
Reactant	(Chloromethyl)cyclopropane	HCID 80013	—
Reactant	2-Bromo-1-ethoxy-4-(methylsulfonyl)benzene	HCID 118022663	—
Reactant	2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroisoquinolin-1-one	HCID 123801900	—
Product	US10023592, Example 216	HCID 118022012	—
Product	2-Bromo-1-ethoxy-4-(methylsulfonyl)benzene	HCID 118022663	—

Reaction Steps

2-bromo-1-ethoxy-4-methanesulfonylbenzene was prepared in a similar manner as Example 46, step 1 except that iodoethane was substituted for (chloromethyl)cyclopropane. The title compound of Example 163, step 3 and 2-bromo-1-ethoxy-4-methanesulfonylbenzene were reacted in a similar manner as in Example 89, step 2 to give the title compound. 1H NMR (CDCl3, 400 MHz): δ 7.92 (dd, J1=8.8 Hz, J2=2.0 Hz, 1H), 7.68 (d, J=2.0 Hz, 1H), 7.03 (d, J=8.8 Hz, 1H), 6.69 (d, J=8.8 Hz, 1H), 4.20 (q, J=7.2 Hz, 2H), 3.59 (s, 3H), 3.08 (s, 3H), 2.70-2.60 (m, 2H), 2.33-2.18 (m, 2H), 1.65-1.61 (m, 4H), 1.45-1.02 (t, J=7.2 Hz, 3H). LCMS: 362.0 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115114B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-b63e90c6757f435db36672e1a262c5be
Source note	uspto-grants-2015_08