Ammonium formate → 7-Hydroxy-4-(2-methylindol-5-yloxy)quinazoline

HRID 454087Notes

Reaction equation

HRID 454087 reaction equation
C([O-])=O.[NH4+].C([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]([O:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28]([CH3:33])=[CH:27]4)=[N:18][CH:19]=[N:20]2)=[CH:15][CH:14]=1)C1C=CC=CC=1>[Pd].CN(C=O)C>[OH:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17]([O:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[NH:29][C:28]([CH3:33])=[CH:27]4)=[N:18][CH:19]=[N:20]2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 220307817-Benzyloxy-4-(2-methylindol-5-yloxy)quinazoline

Product 1

HCID 1357631147-Hydroxy-4-(2-methylindol-5-yloxy)quinazolineYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

10% Palladium on charcoal (200 mg) followed by ammonium formate (4.34 g, 69 mmol) were added to a solution of 7-benzyloxy-4-(2-methylindol-5-yloxy)quinazoline (1.75 g, 4.58 mmol) in DMF (60 ml). After stirring for 1 hour at ambient temperature, the mixture was filtered. The filtrate was evaporated. The residue was triturated with water, filtered, washed with ethyl acetate, and dried under vacuum to give 7-hydroxy-4-(2-methylindol-5-yloxy)quinazoline (1.24 g, 93%).

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was evaporated
  3. customThe residue was triturated with water
  4. filtrationfiltered
  5. washwashed with ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-abafa1972a044234b5d7e5e735c73d04
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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