Pyridine → 2-(3-bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)isoindoline-1,3-dione

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Reaction Steps

A solution of Br2 (30.2 mg, 0.189 mmol) in CH2Cl2 (2.0 mL) was added dropwise over a period of 4 min. to a stirred and cooled (0° C.) solution of 41 (50 mg, 0.189 mmol) and pyridine (18.0 mg, 0.23 mmol) in CH2Cl2 (2 mL). After additional stirring at 0° C. for 26 min. the reaction mixture was treated with a 1:1 (v/v) solution of saturated aqueous NaHCO3 and saturated aqueous Na2S2O3. Stirring continued for 30 min at 0° C. and the organic phase was separated. The aqueous layer was extracted with CH2Cl2. The combined organic solutions were dried (MgSO4), concentrated and the residue was separated by LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—MeCN (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to afford 42 (64.7 mg, quant.). 1H NMR (400 MHz; CDCl3+3 drops of CD3OD) δ 7.40 (s, 1H), 7.81 (dd, J=3.1, 5.4 Hz, 2H), 7.94 (d, J=2.3 Hz, 1H), 7.96 (dd, J=5.5, 3.1 Hz, 2H), 8.29 (d, J=2.3 Hz, 1H); MS (ES) m/z 383 (MH++MeCN).

Provenance & Evidence