Sodium Bicarbonate → ethyl 3-amino-7-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

反応式

Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:10].Cl.[CH2:12]([O:14][C:15](=[O:18])[CH2:16][NH2:17])[CH3:13].C(=O)([O-])O.[Na+]>>[CH2:12]([O:14][C:15]([C:16]1[NH:17][C:2]2[C:3]([Cl:10])=[CH:4][N:5]=[CH:6][C:7]=2[C:8]=1[NH2:9])=[O:18])[CH3:13]

参加物

反応物 3

HCID 516892Sodium Bicarbonate

HCID 2723640Glycine ethyl ester, hydrochloride

HCID 197757134,5-Dichloronicotinonitrile

生成物 1

HCID 59596637ethyl 3-amino-7-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

実験手順

A mixture of 4,5-dichloronicotinonitrile (3.0 g, 17.3 mmol), glycine ethyl ester hydrochloride (7.2 g, 52.0 mmol) and sodium hydrogen carbonate (9.06 g, 104 mmol) in IMS (50 ml) was heated at reflux for 16 hours. The cooled reaction mixture was then partitioned between ethyl acetate and water, the organic layer washed with water then brine, dried (MgSO4) filtered and concentrated in vacuo. The resultant residue was triturated in diethyl ether to give the title compound as a buff solid (3.58 g, 86%). 1H NMR (CDCl3) 8.80 (1H, s), 8.36 (1H, s), 4.97 (2H, s, br), 4.44 (2H, q, J=7.0 Hz), 1.44 (3H, t, J=7.0 Hz).