Iodine → 4-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-2-iodo-quinoline

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Reaction Conditions

Reaction Steps

Diisopropylamine (0.052 ml, 0.5 mmol) was added to a 50 ml round bottomed flask containing tetrahydrofuran (5 ml) and magnetically stirred. The flask was cooled to 0° C. and butyllithium (0.146 ml, 2.5M solution in hexane, 0.5 mmol) was added drop wise. After 10 mins the contents were cooled to −78° C. and 4-(2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-quinoline from Step A (0.100 g, 0.37 mmol) in 20 ml of tetrahydrofuran was added over 15 mins. The stirring was continued for an additional 2 hrs, after which iodine (0.086 g, 0.38 mmol) in 10 ml tetrahydrofuran was added. The reaction mixture was maintained at −78° C. for 2 hrs. Water and tetrahydrofuran (5 ml, 1:9) were added. The reaction mixture was diluted with ethyl acetate, washed with water and brine. Purification by column over silica gel gave pure title compound (0.97 g, 65%). MS (ES) 393.1 (M+H)+

Provenance & Evidence