N-Methyloxindole → HCID 21717225, compound

HRID 1386244Notes

Reaction equation

HRID 1386244 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH3:25])=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1.[CH3:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][C:28]1=[O:36]>C1(C)C=CC=CC=1.C1COCC1>[CH3:23][O:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][C:18]=1[O:24][CH3:25])[N:15]=[CH:14][N:13]=[C:12]2[CH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:27]([CH3:26])[C:28]1=[O:36]

Participants

6

Reactant 3

HCID 6096N-MethyloxindoleHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 21717225HCID 21717225, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium bis(trimethylsilyl)amide (5 ml of a 0.5M solution in toluene, 2.5 mmol) was rapidly added at ambient temperature to a solution of 4-chloro-6,7-dimethoxyquinazoline (337 mg, 1.5 mmol) and 1-methyloxindole (368 mg, 2.5 mmol), (prepared according to the method described in J. Am. Chem. Soc 1945, 67, 1656), in THF (30ml). After 30 minutes, the precipitate was collected by filtration and washed with ether. A second precipitate was isolated from the filtrate. The two solids were mixed and purified by column flash chromatography using methylene chloride/methanol (96/4 and 94/6) as eluent. During the evaporation of the solvents, the compound crystallised. The solid was filtered off, washed with ether and dried under vacuum to give 6,7-dimethoxy-4-(1-methyloxindol-3-yl)quinazoline (103 mg, 20%) as red orange needles.

Workup

  1. custom(prepared
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with ether
  4. customA second precipitate was isolated from the filtrate
  5. additionThe two solids were mixed
  6. custompurified by column flash chromatography
  7. customDuring the evaporation of the solvents
  8. customthe compound crystallised
  9. filtrationThe solid was filtered off
  10. washwashed with ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-516bde44ce12400eb47b4ed2f340a271
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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