Ethyl Bromide → 2-Ethylthieno[2,3-b]pyridine
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[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[Li][C:11](C)(C)[CH3:12].BrCC>C1COCC1.CCOC(C)=O>[CH2:11]([C:2]1[S:1][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1)[CH3:12][S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[Li][C:11](C)(C)[CH3:12].BrCC>C1COCC1.CCOC(C)=O>[CH2:11]([C:2]1[S:1][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1)[CH3:12]To a solution of thieno[2,3-b]pyridine (0.35 g, 2.6 mmoles) prepared according to well known methods [see, Klemm, et al. (1969) J. Org. Chem., 34:347-354; see, also U.S. Pat. Nos. 5,026,700, 4,577,014, 4,406,898, 4,375,544, 4,311,845, and 4,161,599] in THF (10 ml) at −78° C. was added t-BuLi (1.7 M, 2.0 ml, 3.4 mmoles). The reaction solution was slowly warmed to −30° C. over a 45 minute period followed by the addition of bromoethane (0.25 ml, 3.4 mmoles). The solution was stirred 2 hours at ambient temperature then diluted with EtOAc (50 ml) and washed with H2O (75 ml). The organic phase was dried (MgSO4), filtered and concentrated to collect 0.41 g (97%) of the title compound as an orange-brown oil.
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