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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1676247Generated: October 30, 2026

N,N-diethyl-2-methylbut-3-yn-2-amine → 4-(2-(3-(Diethylamino)-3-methylbut-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

https://huagongshe.com/reaction/1676247

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN,N-diethyl-2-methylbut-3-yn-2-amineHCID 13028935—
Reactant3-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)anilineHCID 58474950—
Product4-(2-(3-(Diethylamino)-3-methylbut-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineHCID 6734882832.7%

Reaction Conditions

Temperature50 °C

Reaction Steps

Prepared from N,N-diethyl-2-methylbut-3-yn-2-amine (21 mg, 0.15 mmol) and 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 39 mg, 0.10 mmol) using the procedure described for Example 6, Step B, except the reaction was heated to 50° C. for 24 hours. The crude was purified by preparative TLC (10% MeOH/CH2Cl2). The product was obtained as a waxy solid (13 mg, 31%). 1H NMR (400 MHz, CDCl3) δ 8.47 (m, 1H), 7.51 (s, 1H), 7.02 (m, 1H), 6.49 (m, 3H), 3.85 (s, 2H), 2.76 (m, 4H), 1.52 (s, 6H), 1.14 (m, 6H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08003662B2
Source datasetuspto-grants-2011_08
ORD IDord-208908b2ab7c4890a27ded263d57b3bd
Source noteuspto-grants-2011_08