Dimethylformamide → Methyl 2-amino-5-methoxy-thieno[2,3-b]pyridine-2-carboxylate

반응식

Cl[C:2]1[C:7]([C:8]#N)=[CH:6][C:5]([O:10][CH3:11])=[CH:4][N:3]=1.[C:12]([O:16][CH3:17])(=[O:15])[CH2:13][SH:14].CC([O-])(C)C.[K+].C1COCC1.C[N:30](C=O)C>>[NH2:30][C:13]1([C:12]([O:16][CH3:17])=[O:15])[S:14][C:2]2=[N:3][CH:4]=[C:5]([O:10][CH3:11])[CH:6]=[C:7]2[CH2:8]1

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 16907Methyl Thioglycolate

HCID 128520192-Chloro-5-methoxynicotinonitrile

HCID 66863523KOtBu THF

생성물 1

HCID 18796830Methyl 2-amino-5-methoxy-thieno[2,3-b]pyridine-2-carboxylate수율 71%

실험 절차

To 2-chloro-3-cyano-5-methoxypyridine (0.53 g) and methyl thioglycolate (280 μL) in DMF (10 mL) at 5° C. was added a 1.0M solution of KOtBu/THF (3.8 mL). The reaction was stirred 20 min at 5°, then 2 h at RT, quenched in sat'd NH4Cl, the solid precipitate was collected, washed with water and dried to give 0.53 g (71%) of the title compound.