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Potassium Carbonate → 7-Benzyloxy-4-(2-methylindol-5-yloxy)quinazoline

HRID 1791619
Notes
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Reaction equation

HRID 1791619 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([CH3:30])=[CH:24]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:20][C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[NH:26][C:25]([CH3:30])=[CH:24]4)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 833362-methyl-1H-indol-5-olHCID 220309237-(Benzyloxy)-4-chloroquinazoline

Product 1

HCID 220307817-Benzyloxy-4-(2-methylindol-5-yloxy)quinazolineYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 7-benzyloxy-4-chloroquinazoline (2 g, 7.4 mmol), 5-hydroxy-2-methylindole (1.3 g, 8.9 mmol), (prepared as described for the starting material in Example 48), in DMF (20 ml) containing potassium carbonate (1.53 g, 11.1 mmol) was stirred at 80° C. for 3 hours. After cooling, the mixture was poured in portions into ice/water. The precipitate was filtered and washed with water and dried under vacuum. The solid was dissolved in methylene chloride and was purified by column chromatography eluting with ethyl acetate and methylene chloride (1/1) to give 7-benzyloxy-4-(2-methylindol-5-yloxy)quinazoline (2.28 g, 81%).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum
  5. dissolutionThe solid was dissolved in methylene chloride
  6. customwas purified by column chromatography
  7. washeluting with ethyl acetate and methylene chloride (1/1)

Sources & evidence

ORD record
ord-08ed20305afe40bbb64522a1ad4d9b3c
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