Sodium hydride → HCID 9927113, compound

HRID 1386279Notes

Reaction equation

HRID 1386279 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[H-].[Na+].Cl[C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH3:27])=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1>C1COCC1>[CH3:25][O:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][C:20]=1[O:26][CH3:27])[N:17]=[CH:16][N:15]=[C:14]2[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]1=[O:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 321710OxindoleHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 9927113HCID 9927113, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of oxindole (266 mg, 2.0 mmol) in THF (2 ml) was added dropwise under nitrogen to a stirred suspension of sodium hydride (80 mg, of a 60% dispersion in mineral oil, 2.0 mmol) in THF (1 ml). After stirring the resulting mixture for 15 minutes at ambient temperature, a solution of 4-chloro-6,7-dimethoxyquinazoline (449 mg, 2.0 mmol), (prepared as described for the starting material in Example 1), in THF (20 ml) was added. The mixture was stirred at ambient temperature for 2 hours, quenched with water and the volatiles removed by evaporation. The resulting solid was purified by flash chromatography eluting with methylene chloride/methanol (19/1). The purified product was triturated with methanol, collected by filtration, washed with ether and dried under vacuum to give 6,7-dimethoxy-4-(oxindol-3-yl)quinazoline (77 mg, 12%).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at ambient temperature for 2 hours
  3. customquenched with water
  4. customthe volatiles removed by evaporation
  5. customThe resulting solid was purified by flash chromatography
  6. washeluting with methylene chloride/methanol (19/1)
  7. customThe purified product was triturated with methanol
  8. filtrationcollected by filtration
  9. washwashed with ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-ec8af9d5d01747c19940a9e097a755b7
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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