Water → 4-(Indol-6-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

HRID 454097Notes

Reaction equation

HRID 454097 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:22][C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=[CH:28][NH:29]2)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[NH:29]1[C:30]2[C:26](=[CH:25][CH:24]=[C:23]([O:22][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)[CH:31]=2)[CH:27]=[CH:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5245086-HydroxyindoleHCID 218748234-Chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

Product 1

HCID 220308634-(Indol-6-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazolineYield 50.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-chloro-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (200 mg, 0.6 mmol), (prepared as described for the starting material in Example 50), and 6-hydroxyindole (97 mg, 0.73 mmol) in DMF (3 ml) containing potassium carbonate (125 mg, 0.91 mmol) was heated at 90° C. for 2.5 hours. After cooling, water was added. The precipitate was filtered, washed with water and dried under vacuum. The residue was triturated with ether, filtered, washed with ether and dried under vacuum to give 4-(indol-6-yloxy)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (130 mg, 50%).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum
  5. customThe residue was triturated with ether
  6. filtrationfiltered
  7. washwashed with ether
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a8e8dfd7cbf04df7ac6e8028a96886b6
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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