Reaction #324433

Reaction equation

3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

title compound

5-Bromomethyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester

Cs2CO3

→

title compound

Yield 71.2%

3-[5-Chloro-2-(4-ethoxycarbonyl-5-trifluoromethyl-furan-2-ylmethoxy)-phenoxy]-azetidine-1-carboxylic acid tert-butyl ester

Yield 71.2%

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe title compound was prepared
2. 2
   OtherThe crude material was purified by RP HPLC

Procedure

The title compound was prepared as described in Example 1 Step D using 3-(5-chloro-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (0.3 g, 1.0 mmol), the title compound of Example 75 Step A (0.75 g, 2.5 mmol), Cs2CO3 (0.80 g, 2.4 mmol) and KI (0.23 g, 1.4 mmol) in DMF (15 mL). The crude material was purified by RP HPLC to provide the title compound (0.37 g, 71%). 1H NMR (CDCl3): 7.20-6.92 (m, 1H), 6.91-6.80 (m, 2H), 6.77-6.69 (m, 1H), 6.53 (d, J=2.1 Hz, 1H), 4.87 (s, 2H), 4.79-4.69 (m, 1H), 4.27-4.12 (m, 2H), 4.00-3.88 (m, 2H), 1.38 (s, 9H).

Source