Dimethylformamide → HCID 21717265, compound

HRID 1386272Notes

Reaction equation

HRID 1386272 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1.CN(C=O)C>C1COCC1>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH3:28])[N:18]=[CH:17][N:16]=[C:15]2[CH:6]1[C:5]2[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[NH:8][C:7]1=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 37310136-fluoro-2,3-dihydro-1H-indol-2-one

Product 1

HCID 21717265HCID 21717265, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-fluorooxindole (264 mg, 1.75 mmol), (prepared according to Synthesis 1993, 51), in THF (3 ml) was added dropwise under nitrogen to sodium hydride (42 mg, 1.75 mmol, pre-washed with hexane). After stirring the resulting mixture for 20 minutes at ambient temperature, 4-chloro-6,7-dimethoxyquinazoline (210 mg, 0.93 mmol), (prepared as described for the starting material in Example 1), was added as a solid, followed by DMF (4 ml). The reaction mixture was then heated at 85° C. for 1 hour, the solvent was removed by evaporation and the residue partitioned between ether and water. The aqueous layer was separated and neutralised with 2M hydrochloric acid and the solid was collected by filtration, washed with ether and dried under vacuum to give 6,7-dimethoxy4-(6-fluorooxindol-3-yl)quinazoline (255 mg, 81%) as a yellow solid.

Workup

  1. additionwas added as a solid
  2. temperatureThe reaction mixture was then heated at 85° C. for 1 hour
  3. customthe solvent was removed by evaporation
  4. customthe residue partitioned between ether and water
  5. customThe aqueous layer was separated
  6. filtrationthe solid was collected by filtration
  7. washwashed with ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-efe1175837714f39a5e919f8bb896858
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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