C([N-]C(C)C)(C)C.[Li+].N[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]1[CH:30]=[CH:29][CH:28]=[CH:27][C:17]=1[C:18]([N:20](C(C)C)C(C)C)=[O:19]>C1COCC1>[CH:12]1[N:13]=[CH:14][CH:15]=[C:10]2[C:11]=1[C:16]1[CH:30]=[CH:29][CH:28]=[CH:27][C:17]=1[C:18](=[O:19])[NH:20]2A solution of lithium diisopropyl amide (LDA, 2.0 M, Aldrich, 10 mL) was dissolved in 90 mL of THF and cooled to −78° C. A solution of amine 3 (2.0 g, 6.73 mmol) in THF (25 mL) was added to the LDA dropwise over a 15 minute period. The reaction was warmed to room temperature and stirred overnight. The reaction was concentrated in vacuo and suspended in 100 mL water. The solid was filtered off and triturated with ethyl acetate (100 mL). The resulting solid was dried to yield 1.24 g (94%) of the desired compound 4. An analytical sample can be obtained by recrystallization with copious amounts of methanol. 1H NMR (DMSO): δ 9.57 (s, 1H), 8.65 (d, 1H), 8.50 (d, 1H), 8.33 (d, 1H), 7.90 (t, 1H), 7.71 (t, 1H), 7.28 (d, 1H). Anal Calcd for C12H8N2O: C, 73.46; H, 4.11; N, 14.28. Found: C, 73.53; H, 4.26; N, 14.37.
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