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Potassium Carbonate → 4-(6-Fluoroindol-5-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline

HRID 1791765
Notes
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Reaction equation

HRID 1791765 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:24][C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[CH:30][NH:31]2)=[CH:27][C:26]=1[OH:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:24][C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[CH:30][NH:31]2)=[CH:27][C:26]=1[O:34][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110021914-Chloro-6-methoxy-7-(3-(piperidin-1-YL)propoxy)quinazolineHCID 220309296-Fluoro-1H-indol-5-ol

Product 1

HCID 220307274-(6-Fluoroindol-5-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazolineYield 46.6%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-chloro-6-methoxy-7-(3-piperidinopropoxy)quinazoline (222 mg, 0.662 mmol), (prepared as described for the starting material in Example 67), and 6-fluoro-5-hydroxyindole (120 mg, 0.794 mmol), (prepared as described for the starting material in Example 242), in DMF (3 ml) containing potassium carbonate (137 mg, 0.993 mmol) was heated at 95° C. for 3.5 hours. After cooling the mixture was poured onto water and extracted with ethyl acetate. The organic layers were washed with water, brine, dried (MgSO4) and evaporated. The residue was triturated with ether, filtered and dried under vacuum to give 4-(6-fluoroindol-5-yloxy)-6-methoxy-7-(3-piperidinopropoxy)quinazoline (139 mg, 46%).

Workup

  1. custom(prepared
  2. custom(prepared
  3. temperatureAfter cooling the mixture
  4. additionwas poured onto water
  5. extractionextracted with ethyl acetate
  6. washThe organic layers were washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was triturated with ether
  10. filtrationfiltered
  11. customdried under vacuum

Sources & evidence

ORD record
ord-04597e881e554ce1a6de9893aef3d4a7
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074800B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes