Ethyl bromoacetate → Ethyl {[6-cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-2-methyl-5,6,7,8-tetrahydro quinazolin-4-yl]oxy}acetate

HRID 2383989Notes

Reaction equation

HRID 2383989 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([C:16]2([C:28]#[N:29])[CH2:25][CH2:24][C:23]3[N:22]=[C:21]([CH3:26])[NH:20][C:19](=[O:27])[C:18]=3[CH2:17]2)=[CH:5][CH:4]=1.[CH2:30]([O:32][C:33](=[O:36])[CH2:34]Br)[CH3:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[C:28]([C:16]1([C:6]2[C:7]3[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[O:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:25][CH2:24][C:23]2[N:22]=[C:21]([CH3:26])[N:20]=[C:19]([O:27][CH2:34][C:33]([O:32][CH2:30][CH3:31])=[O:36])[C:18]=2[CH2:17]1)#[N:29]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 1356204916-(4-Methoxydibenzo[b,d]furan-1-yl)-2-methyl-4-oxo-3,4,5,6,7,8-hexahydroquinazoline-6-carbonitrile

Product 1

HCID 24804611Ethyl {[6-cyano-6-(4-methoxydibenzo[b,d]furan-1-yl)-2-methyl-5,6,7,8-tetrahydro quinazolin-4-yl]oxy}acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in example 21 (150 mg, 1.76 mmles) in dry DMF (5 ml) was added ethylbromoacetate (322.3 mg, 1.93 mmol) and cesium carbonate (688 mg, 2.11 mmol). The reaction mass was stirred at room temperature for 1 hr, diluted with water and extracted with ethyl acetate. The organic layer was washed with water followed by brine and dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography to get both pure compounds.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by column chromatography
  6. customto get both pure compounds

Sources & evidence

ORD record
ord-9059a38c5f844c03b8cf23c6b9fb767b
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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