Reaction #2329006

Reaction equation

N-(2-fluoroethyl)-5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine

hydrobromic acid

→

title compound

Yield 21.1%

2-{6-[(2-Fluoroethyl)amino]pyridin-3-yl}-1,3-benzoxazol-6-ol

Yield 21.1%

Solvents

NaHCO3

Conditions

Workup

1. 1
   OtherThe reaction vessel was sealed
2. 2
   Extractionextracted with (3×50 mL) CH2Cl2
3. 3
   Dryingthe combined organic layers were dried (Na2SO4)
4. 4
   Otherevaporated
5. 5
   Otherto give 33.1 mg as a brown oil
6. 6
   OtherPurified on prep HPLC

Procedure

To N-(2-fluoroethyl)-5-(6-methoxy-1,3-benzoxazol-2-yl)pyridin-2-amine (0.18 mmol), in a microwave vial with a stir bar, was added tetrabutylammonium bromide (0.02 mmol) and hydrobromic acid 48%, w/w aq soln (5.0 mL). The reaction vessel was sealed and heated at 120° C. for 10 min. LCMS showed remaining starting material and the reaction was run an additional 10 min. The reaction mixture was neutralized with sat NaHCO3 (100 mL), extracted with (3×50 mL) CH2Cl2, the combined organic layers were dried (Na2SO4) and evaporated to give 33.1 mg as a brown oil. Purified on prep HPLC to give 10.4 mg of the title compound as a tan solid after lyophilization. 1H NMR (400 MHz, Chloroform-d/MeOH-d4 1:1) δ ppm 8.75 (d, 1H) 8.05 (dd, 1H) 7.42 (d, 1H) 7.00 (d, 1H) 6.82 (dd, 1H) 6.63 (d, 1H) 4.62-4.66 (m, 1H) 4.50-4.54 (m, 1H) 3.71-3.76 (m, 1H) 3.64-3.69 (m, 1H); 19F (1H decoupled) NMR (400 MHz, Chloroform-d/MeOH-d4) δ ppm −224.8; MS m/z 274 (M+H).

Source