Sodium Hydroxide → HCID 66758161, compound

Participants

Reaction Steps

7-Bromo-1-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole (11 in scheme 2 wherein R2═OCH3): A solution of 7-bromo-1H-indole (0.30 g, 1.53 mmol) in glacial acetic acid (1.5 mL) was treated with sodium cyanoborohydride (0.14 g, 2.29 mmol) under N2 at 0° C. After aqueous sodium hydroxide solution was added to quench excess acid, the resulting mixture was then extracted with CH2Cl2 (20 mL×3). The combined organic layers were dried over MgSO4, the dried solution was filtered, and the filtrate was concentrated. The residue was dissolved in pyridine and 4-methoxyphenylsulfonyl chloride was added. The reaction mixture was refluxed overnight. The solvent was removed and the residue was purified by flash chromatography (EtOAc: n-hexane=1:2) to afford 11 (370.6 mg, 87%).

Provenance & Evidence