[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=O.[NH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][N:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]13-Amino-pyridine-4-carbaldehyde (5.00 g, 40.9 mmol) was dissolved in DCM (60 mL), ethyl 4-piperidinecarboxylate (7.57 mL, 49.1 mmol) and NaBH(OAc)3 (10.4 g, 49.1 mmol) were added and the reaction mixture was heated in a microwave reactor at 60° C. for 5 min. The reaction mixture was diluted with DCM (100 mL) and quenched with sat aq Na2CO3 (50 mL). The organic fraction was washed with sat aq NH4Cl (30 mL). The combined aq fractions were extracted with DCM (2×50 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow gum (11.3 g). LCMS (ES+): 264.1 [MH]+.
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