Dichloromethane → 4-(Cyclopropylethynyl)-3-fluoroaniline

To a stirred solution of 4-iodo 3-fluoro aniline (2.25 g, 9.49 mmol) in THF (25 ml) at 0° C. to −5° C., CuI (90 mg, 0.47 mmol) and Et3N (3.5 ml, 25.62 mmol) were added. The reaction mixture was deoxygenated by purging with a stream of Argon for 30 minutes at −5° C. Addition of Pd(dppf)Cl2.CH2Cl2 (346 mg, 0.47 mmol) and purging was continued. After 10 minutes, cyclopropyl acetylene (0.72 ml, 8.54 mmol) was added at −5° C. and stirred at room temperature for 16 h. The reaction mixture was diluted with ether (200 mL), filtered through celite pad, washed with ether (2×25 mL). The filtrate was concentrated and the residue purified by column chromatography (100-200 mesh silica gel) using hexane as eluent to afford title compound as pale brown liquid (750 mg, 45%).

1. customThe reaction mixture was deoxygenated
2. customby purging with a stream of Argon for 30 minutes at −5° C
3. additionAddition of Pd(dppf)Cl2
4. filtrationfiltered through celite pad
5. washwashed with ether (2×25 mL)
6. concentrationThe filtrate was concentrated
7. customthe residue purified by column chromatography (100-200 mesh silica gel)

ORD record

ord-401f74a8b1e344ca82a15afcda5a523b

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592471B2