[H-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[O:10][C:6]=2[CH:5]=1.I[CH2:15][CH2:16][CH3:17]>CN(C=O)C>[F:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH2:15][CH2:16][CH3:17])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=1To 670 mg (16.74 mmol) of hexanes washed sodium hydride in 20 ml DMF was added a solution of 2.33 g (15.22 mmol) 6-fluoro-1,3-benzoxazolin-2(3H)-one in 40 ml DMF. The reaction was stirred for 10 minutes before 3.11 g (18.3 mmol) 1-iodopropane was added and then stirred for 3 hr at room temperature. After quenching onto 50 ml of ice/water, the aqueous phase was extracted with EtOAc (2×100 ml). The combined organic layers were washed with water (1×100 ml), dried over Na2SO4 and evaporated to dryness in vacuo to give 2.2 g (75% yield) of the alkylated product as a brown solid.
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