5-cyclopropyl-3,4-dihydro-1H-quinolin-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one (147-5; 0.5 g, 0.00267 mol) in N,N-dimethylformamide (10 mL) was added N-bromosuccinimide (0.47 g, 0.0026 mol) portion wise at 0° C. Reaction mixture was allowed to stir at room temperature for 4 h. The reaction mixture was concentrated and diluted with ice cold water (100 mL) with constant stirring, the solid residue obtained was filtered and dried to obtain the title compound. MS (M+1): 266.1. Reaction mixture The reaction mixture was concentrated diluted with ice cold water (100 mL) with constant stirring the solid residue obtained was filtered dried

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 5-chloro-3,4-dihydroquinolin-2(1H)-one (147-4; 1 g, 0.0055 mol) and cyclopropylboronic acid (0.95 g, 0.0110 mol) in tetrahydrofuran (30 mL) was added potassium phosphate (3.4 g, 0.0165 mol) and S-Phos (0.45 g, 0.0011 mol). Reaction mass was purged with argon for 20 min. Then catalyst palladium acetate (0.123 g, 0.00055 mol) was added and allowed to stir at 120° C. for 12 h. The reaction mixture was filtered through CELITE bed and filter bed was thoroughly washed with ethyl acetate. The collected organic part was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography to obtain title compound. MS (M+1): 188.1. Reaction mass was purged with argon for 20 min The reaction mixture was filtered through CELITE bed filter bed was thoroughly washed with ethyl acetate The collected organic part was concentrated under vacuum to afford the crude compound, which was purified by silica gel column chromatography