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

HRID 52014Notes

Reaction equation

HRID 52014 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

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 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.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue obtained by concentration under reduced pressure
  5. customwas crystallized with isopropyl ether

Sources & evidence

ORD record
ord-a27712b0f6a2409f9d9fe02c132d3342
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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