HCID 22030824, compound → 7-hydroxy-4-(1H-indol-5-yloxy)-6-methoxyquinazoline

HRID 1791628Notes

Reaction equation

HRID 1791628 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[CH:23]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:29][CH3:30])C1C=CC=CC=1.[H][H]>CN(C=O)C.C(Cl)Cl.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[CH:23]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:29][CH3:30]

Participants

6

Reactant 2

HCID 22030824HCID 22030824, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1357631167-hydroxy-4-(1H-indol-5-yloxy)-6-methoxyquinazolineYield 44%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7-benzyloxy-4-(indol-5-yloxy)-6-methoxyquinazoline (8 g, 20 mmol) in DMF (50 ml) and methylene chloride (100 ml) containing 10% palladium on charcoal (2 g) was hydrogenated at 1.8 atmospheres pressure until uptake of hydrogen had ceased. The solution was filtered, the catalyst was washed with DMF and the filtrate was evaporated. The residue was purified by column chromatography eluting with methylene chloride, followed by methylene chloride/methanol (95/5 and 90/10). After evaporation of the solvent, the residue was triturated with ether, filtered and dried under vacuum to give 7-hydroxy-4-(indol-5-yloxy)-6-methoxyquinazoline (2.7 g; 44%).

Workup

  1. filtrationThe solution was filtered
  2. washthe catalyst was washed with DMF
  3. customthe filtrate was evaporated
  4. customThe residue was purified by column chromatography
  5. washeluting with methylene chloride
  6. customAfter evaporation of the solvent
  7. customthe residue was triturated with ether
  8. filtrationfiltered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-7667d085405e46f48417935fc1ca117f
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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