Triethylamine → 6-Azaindole
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Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.CCN(CC)CC.[H][H]>CO.[Pd]>[NH:8]1[C:7]2=[CH:2][N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9]1Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.CCN(CC)CC.[H][H]>CO.[Pd]>[NH:8]1[C:7]2=[CH:2][N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9]1A mixture of Example 695H (3.6 g, 23.6 mmol), Pd/C (0.5 g, 5%), and Et3N (2.3 g, 23.6 mmol) in MeOH (100 mL) was stirred under a balloon of hydrogen at room temperature overnight. The reaction mixture was filtered through diatomaceous earth (Celite®), and the solid was washed with additional MeOH. The solvent was removed to near dryness, and the semi-solid was treated with 300 mL of EtOAc. The precipitate was removed right away by filtration, and the filtrate was concentrated. The residue was re-dissolved in CH2Cl2, and loaded onto a silica gel column eluted with 100/5:0/5 (EtOAc/MeOH/NH4OH) to give 2.7 g (100%) of the desired product. MS (DCI) m/e 119 (M+H)+, 1H NMR (300 MHz, DMSO-d6): □ 11.6 (br s, 1H), 8.76 (dd, J=1.0, 1.0 Hz, 1H), 8.08 (d, J=5.4 Hz, 1H), 7.60 (d, J=3.0 Hz, 1H), 7.53 (dd, J=5.4, 1.0 Hz, 1H), 6.50 (dd, J=3.0, 1.0 Hz, 1H).
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