(5-methyl-1,3,4-oxadiazol-2-yl)acetonitrile(SALTDATA: FREE) synthesis

Yield: 44%

Reaction Conditions:

with trichlorophosphate in toluene at 80; for 2.5 h;

Steps:

2-(5-methyl-l,3,4-oxadiazol-2-yl)acetonitrile
Intermediate 163 (90%, 2.8 g, 17.86 mmol) was stirred in toluene (75 mL). POCI₃ (4.55 g, 29.68 mmol) was added and the suspension was heated at 80 °C for 2.5 hours. The reaction was allowed to cool and the suspension was added to water (100 mL) then taken to pH7 using saturated aq. Na CC> . The aqueous solution was extracted with ethyl acetate (3 x 100 mL), the organics were dried over sodium sulfate and concentrated in vacuo to afford the title compound (980 mg, 44%) as a red solid. d_H (500 M Hz, Chloroform-d) d 4.02 (s, 2H), 2.58 (s, 3H). dH (500 MHz, DMSO-d₆) d 4.57 (s, 2H), 2.51 (s, 3H).

References:

UCB BIOPHARMA SRL;CHOVATIA, Prafulkumar Tulshibhai;CONNELLY, Rickki Lee;FRANKLIN, Richard Jeremy;HASLETT, Gregory William;HENRY, Alistair James;MADDEN, James;NEUSS, Judi Charlotte;NORMAN, Timothy John;PHILPS, Oliver;PITT, William Ross;RAMPALAKOS, Konstantinos;SELBY, Matthew Duncan;SELVARATNAM, Suganthan;TRANI, Giancarlo;ZHU, Zhaoning WO2019/243550, 2019, A1 Location in patent:Page/Page column 233; 234