Toluene → (cis) (4-(4-Chloroindolin-1-yl)thiazol-2-yl) (2,6-dimethylmorpholino) methanone

Participants

Reaction Conditions

Reaction Steps

(cis) (4-bromothiazol-2-yl) (2,6-dimethylmorpholino)methanone (step-1 of compound 45, 1.0 g, 3.28 mmol) and 4-chloroindoline (0.55 g, 3.60 mmol) were added to seal tube containing toluene (25 ml). Sodium tert-butoxide (0.47 g. 4.91 mmol) was added, the nitrogen gas was bubbled through reaction mixture for 15 minutes and tris(dibenzylideneacetone)dipalladium(0) (0.15 g, 0.16 mmol) was added under nitrogen and the tube was sealed. The reaction mixture was heated at 100° C. for 18 hr under stirring. The progress of reaction was monitored by TLC. The reaction mixture was cooled to 25° C. and diluted with ethyl acetate (100 ml) and washed with water (25 ml). The organic layer was dried over sodium sulfate filtered and concentrated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 15% ethyl acetate in hexanes as an eluent to obtain the title compound (0.75 g, 60.6%). MS: m/z 378 (M+1).

Provenance & Evidence