Carbon Tetrachloride → 3,7-Dichloro-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

反応式

[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2C=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C1C(=O)N([Cl:29])C(=O)C1.C(OOC(C1C=CC=CC=1)=O)(C1C=CC=CC=1)=O.[C:48]([Cl:52])(Cl)(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:21])=[C:8]2[C:48]([Cl:52])=[CH:13][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[C:10]([Cl:29])[N:11]=1)=[O:5])[CH3:2]

参加物

反応物 4

HCID 5943Carbon Tetrachloride

HCID 7187Benzoyl Peroxide

HCID 31398Chlorosuccinimide

HCID 684267014-Hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

生成物 1

HCID 866173533,7-Dichloro-4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

実験手順

A mixture of 4-hydroxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (270 mg, 0.956 mmol), NCS (269 mg, 2.01 mmol) and BzOOBz (12 mg, 0.048 mmol) in carbontetrachloride (4 mL) was refluxed for 30 min. Then the reaction was cooled and concentrated, the resulting mixture was purified by column to give the desired product (173 mg). The title compound, 1H NMR (200 MHz, CDCl3): δ (ppm)=11.8 (s, 1H), 7.6-7.3 (m, 6H), 4.52 (q, 2H, J=6.8 Hz), 1.47 (t, 3H, J=6.8 Hz).