Water → 4-(4-Fluoro-2-methylindol-5-yloxy)-6-hydroxy-7-methoxyquinazoline

HRID 2068014Notes

Reaction equation

HRID 2068014 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][N:13]=[C:12]2[O:21][C:22]1[C:23]([F:32])=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([CH3:31])=[CH:25]2)C1C=CC=CC=1.C([O-])=O.[NH4+].O>[Pd].CN(C=O)C>[F:32][C:23]1[C:22]([O:21][C:12]2[C:11]3[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([OH:8])[CH:10]=3)[N:15]=[CH:14][N:13]=2)=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[C:26]([CH3:31])[NH:27]2

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 666463136-Benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline

Product 1

HCID 112677704-(4-Fluoro-2-methylindol-5-yloxy)-6-hydroxy-7-methoxyquinazolineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline (1.32 g, 3 mmol), ammonium formate (1.94 g, 30 mmol) and 10% palladium on carbon (0.2 g) in DMF (15 ml) containing water (2 ml) was stirred at ambient temperature for 1 hour. The mixture was filtered and the filtrate was evaporated. The residue was triturated under diethyl ether, filtered, washed with diethyl ether followed by water and dried under vacuum over P2O5 overnight to give 4-(4-fluoro-2-methylindol-5-yloxy)-6-hydroxy-7-methoxyquinazoline (1 g, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was triturated under diethyl ether
  4. filtrationfiltered
  5. washwashed with diethyl ether
  6. dry with materialdried under vacuum over P2O5 overnight

Sources & evidence

ORD record
ord-1606ae7c933940f5bd8eab6da7fa16b2
Source dataset
uspto-grants-2012_10
Patent number
US08293902B2

Reaction notes

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