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

HRID 916370Notes

Reaction equation

HRID 916370 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-90e5350c29454f5da92057a594404151
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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