Benzoyl chloride → Benzyl 1-benzoyl-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylate

HRID 52016Notes

Reaction equation

HRID 52016 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])=[C:15]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:14]=3[C:13]=2[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[N:4]=1.[H-].[Na+].[C:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCCC1>[CH2:30]([O:29][C:27]([C:13]1[C:14]2[C:15]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:16]([CH3:21])[N:17]([C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:18]=2[CH:19]=[CH:20][C:12]=1[O:11][C:5]1[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=1)=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 19962802HCID 19962802, compound

Product 1

HCID 19962759Benzyl 1-benzoyl-5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of benzyl 5-[(4,6-dimethoxypyrimidin-2-yl)oxy]-3-ethoxycarbonyl-2-methylindol-4-carboxylate was dissolved in 50 ml of tetrahydrofuran, and 0.176 g of 60% sodium hydride was added thereto. The mixture was stirred at room temperature for 30 minutes. Then, 0.51 g of benzoyl chloride was dropwise added thereto at room temperature, and the mixture was stirred for 4 hours. After concentration under reduced pressure, the mixture 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 from isopropyl ether to obtain 1.67 g (yield: 92%) of the desired compound. mp: 128°-132.5° C.

Workup

  1. stirringat room temperature, and the mixture was stirred for 4 hours
  2. concentrationAfter concentration under reduced pressure
  3. additionthe mixture was poured into ice water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe residue obtained by concentration under reduced pressure
  8. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-d2c12e93f45949b599f2a7f549b49e7c
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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