[O:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[CH3:13]CN=C=NCCCN(C)C.Cl.CO>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:13][O:11][C:10]([C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[O:1][CH:2]=1)=[O:12]To a suspension of furo[2,3-b]pyridine-3-carboxylic acid (53 mmol) in 85 mL DCM were added EDC.HCl (58 mmol), DMAP (16 mmol) and 4.3 mL MeOH. The beige suspension was stirred at RT for 2 h. The reaction mixture was diluted with 50 mL DCM and quenched with sat. aq. NaHCO3 solution. The organic phase was washed 3 times with sat. aq. NH4Cl solution and once with brine. The organic layer was dried over MgSO4 and concentrated in vacuo to obtain the desired compound as grey solid.
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