[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].Br[C:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:14])[C:10]([O:12][CH3:13])=[O:11].C(=O)=O.CO.CC#N>CN(C=O)C>[C:3]([CH:2]([C:1]#[N:5])[C:9]([CH3:14])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:4]
A DMF (7 mL) solution of malononitrile (0.413 g, 6.24 mmol) was added to a suspension of NaH (0.252 g, 6.30 mmol, 60%) in DMF (9 mL) cooled to 0° C. After 10 minutes a DMF (7 mL) solution of the intermediate from Step B (1.438 g, 5.89 mmol) was added. The reaction solution was then stirred overnight at room temperature. The solution was then partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (400 MHz, CHCl3-d): δ 8.59 (d, J=4.8 Hz, 1H); 7.79 (td, J=7.7, 1.8 Hz, 1H); 7.50 (d, J=8.0 Hz, 1H); 7.32 (dd, J=7.6, 4.8 Hz, 1H); 5.25 (s, 1H); 3.77 (s, 3H); 2.01 (s, 3H). m/z=230.2 (M+H). The racemic material was resolved on a Berger SFC II preparative instrument using a ChiralCel IA-H, 250×30 mm I.D. column and a SFC CO2/Methanol/MeCN eluent.
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