2-(Ethylamino)ethanol → 2-(4-(2-(Ethyl(3-fluoropropyl)amino)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol

Participants

Role	Name	HCID	Charge
Reactant	2-(Ethylamino)ethanol	HCID 8072	—
Reactant	1-Iodo-3-fluoropropane	HCID 12899128	—
Reactant	2-(4-iodophenyl)-4-methyl-6-((tetrahydro-2H-pyran-2-yl)oxy)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2H-chromene	HCID 86682885	—
Product	2-(4-(2-(Ethyl(3-fluoropropyl)amino)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol	HCID 89634473	—

Reaction Steps

The title compound was synthesized as described in general procedures F, I and J (z=1) using Intermediate 3 and 2-(ethylamino)ethanol in general procedure F, and 1-fluoro-3-iodopropane in general procedure I. 1H NMR (400 MHz, DMSO-d6): δ 9.43 (s, 1H), 8.94 (s, 1H), 7.19 (d, 2H), 7.13 (t, 1H), 6.78 (d, 2H), 6.76-6.72 (m, 1H), 6.68 (d, 1H), 6.67-6.62 (m, 1H), 6.62-6.60 (m, 1H), 6.48 (s, 2H), 5.84 (s, 1H), 4.50 (t, 1H), 4.39 (t, 1H), 3.91 (t, 2H), 2.72 (t, 2H), 2.58-2.45 (m, 4H), 2.03 (s, 3H), 1.80-1.71 (m, 1H), 1.71-1.65 (m, 1H), 0.93 (t, 3H). LCMS: 478.1 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09193714B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-99ac52240aad45bf856f11350ecd8800
Source note	uspto-grants-2015_11