[NH2:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:5]2=[CH:4][CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+].[CH:19](OCC)(OCC)OCC>CC(O)=O>[N:1]1([C:2]2[N:7]=[C:6]3[CH2:8][CH2:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:5]3=[CH:4][CH:3]=2)[CH:19]=[N:17][N:16]=[N:15]1To a flask charged with methyl 2-amino-6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate (500 mg, 2.6 mmol) and a stir bar was added sodium azide (340 mg, 5.2 mmol), triethyl orthoformate (2.2 mL, 13 mmol), and HOAc (10 mL). The mixture was heated to 100° C. for 2 hours. The solvent was removed on a rotavapor, and the residue was taken into aq. sodium carbonate, extracted with EtOAc (50 mL×3), dried over sodium sulfate, and purified by MPLC (DCM-MeOH). After removal of solvent, the title compound was collected. LC-MS (IE, m/z): 248 [M+1]+.
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