Pyridine → Allyl 3-Acetylamino-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:20]=[CH:19][C:18]3[NH:17][C:16]([CH3:21])=[CH:15][C:14]=3[C:13]=2[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[N:4]=1.[C:28]([O:31]C(=O)C)(=O)[CH3:29].[N:35]1C=CC=CC=1>>[C:28]([NH:35][C:15]1[C:14]2[C:13]([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])=[C:12]([O:11][C:5]3[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=3)[CH:20]=[CH:19][C:18]=2[NH:17][C:16]=1[CH3:21])(=[O:31])[CH3:29]

Participants

Reactant 3

HCID 1049Pyridine

HCID 7918Acetic Anhydride

HCID 19962801Allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate

Product 1

HCID 19962751Allyl 3-Acetylamino-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylateYield 87%

Procedure

0.5 g of allyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-2-methylindol-4-carboxylate was dissolved in 10 ml of pyridine, and 0.16 g of acetic anhydride was added thereto. The mixture was stirred for 12 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized with isopropyl ether to obtain 0.49 g (yield: 87%) of the desired compound. mp: 177°-180° C.