Dimethylformamide → 6-Methoxy-1,3,3-trimethylindolin-2-one

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Reaction Steps

In a flame-dried flask under nitrogen, 490 mg of 60% sodium hydride (12.26 mmol) was slurried three times with Hexanes, and the Hexanes were syringed off. Added 6.25 ml of N,N-dimethylformamide, followed by 500 mg of 6-Methoxy-1,3-dihydro-indol-2-one (3.06 mmol) and stirred at room temperature for 5 minutes. Chilled in ice-H2O bath and added 763 μl of methyl iodide (12.26 mmol) dropwise. After 10 minutes, warmed to room temperature and stirred for 1.5 hours. Chilled in ice-H2O bath and added 20 ml of H2O dropwise. Extracted three times with 2:1 EtOAc/toluene. The combined organics were washed with sodium thiosulfate, H2O and brine, dried (MgSO4) and the solvent removed in vacuo to crude red oil. Purified on Biotage Flash 40, eluting with 4:1 Hexanes/EtOAc to give 285 mg of a white solid (45%). 1H NMR (400 MHz, CDCl3) δ 1.31 (6H, s), 3.16 (3H, s), 3.80 (3H, s), 6.41 (1H, d, J=2.28 Hz), 6.53 (1H, m), 7.06 (1H, d, J=8.1 Hz). M/z (APCI+) 206.0 (M+1).

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