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

Participants

Role	Name	HCID	Charge
Reactant	2-(Ethylamino)ethanol	HCID 8072	—
Reactant	Ethane, 1-fluoro-2-iodo-	HCID 69804	—
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(2-fluoroethyl)amino)ethoxy)phenyl)-3-(3-hydroxyphenyl)-4-methyl-2H-chromen-6-ol	HCID 89634472	—

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-2-iodoethane in general procedure I. 1H NMR (400 MHz, DMSO-d6): δ 9.46 (s, 1H), 8.95 (s, 1H), 7.19 (d, 2H), 7.13 (t, 1H), 6.78 (d, 2H), 6.76-6.71 (m, 1H), 6.78 (d, 1H), 6.78-6.62 (m, 1H), 6.62-6.60 (m, 1H), 6.58 (s, 2H), 5.83 (s, 1H), 4.50 (t, 1H), 4.38 (t, 1H), 3.92 (t, 2H), 2.83-2.77 (m, 3H), 2.74 (t, 1H), 2.58 (q, 2H), 2.03 (s, 3H), 0.94 (t, 3H). LCMS: 464.1 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09193714B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-2be3177ffb2f4bc9a24f930500dfa37e
Source note	uspto-grants-2015_11