Methyl iodide → 3-Bromo-2-methyl-thieno[3,2-c]pyridine
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[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.O1CCC[CH2:12]1.C(NC(C)C)(C)C.[Li].C1CCCCC1.CI>C1COCC1>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[CH3:12][Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.O1CCC[CH2:12]1.C(NC(C)C)(C)C.[Li].C1CCCCC1.CI>C1COCC1>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[CH3:12]291 mg of 3-Bromo-thieno[3,2-c]pyridine (1.36 mmol) is dissolved in 3 ml of dry THF and cooled to −78° C. 1.00 ml of lithium diisopropylamine mono(tetrahydrofuran) 1.5M solution in cyclohexane (1.5 mmol) is added to the mixture at −78° C. and stirred at −78° C. for 20 min. 213 mg of methyl iodide (1.5 mmol) is added to the mixture and stirred at −78° C.→room temperature for 1 h. The reaction mixture is quenched by sat. NH4Cl and extracted with CH2Cl2. The separated CH2Cl2 is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt:2 M NH3 in MeOH=20:4:1) to give 225 mg of the title compound. Yield 72%. mass spectrum (m/e): 230 (M+1); 1H-NMR (CDCl3): 9.01 (s, 1H), 8.52 (d, 1H, J=5.5 Hz), 7.72 (d, 1H, J=5.5 Hz), 2.61 (s, 3H) ppm.
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