Sodium Methoxide → HCID 54209394, compound

Reaction equation

Cl[C:2]1[N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]=[N:16][N:17]([CH3:28])[C:18]2[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1.[CH3:29][O-:30].[Na+]>C1COCC1.O>[CH3:29][O:30][C:2]1[N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH:15]=[N:16][N:17]([CH3:28])[C:18]2[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1

Participants

Procedure

The title compound of Step B (0.38 g, 0.93 mmol) was dissolved in THF (10 mL) and then sodium methoxide (25% in methanol, 0.56 mL) was added dropwise. The mixture was heated at reflux for 1 h, cooled to room temperature and then diluted with water and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to an oil which was purified by flash column chromatography on silica gel to afford 0.27 g of the title compound of Step C, a compound of the invention, as a pale yellow solid melting at 185-187° C. 1H NMR (300 MHz, CDCl3): δ 8.41 (dd,1H, J=5, 1.5 Hz), 8.12 (dd,1H, J=8, 1.5 Hz), 8.01 (dd,1H, J=8, 1.5Hz), 7.42 (m,3H), 7.23 (d,1H J=8 Hz), 15 7.02 (dd,1H, J=8, 5Hz), 3.93 (s,3H), 3.56 (s,3H), 3.48 (s,3H).