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

HRID 2180124Notes

Reaction equation

HRID 2180124 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[C:21]([F:30])=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24]([CH3:29])=[CH:23]4)=[CH:14][N:15]=[N:16]2)=[CH:11][C:10]=1[O:31][CH3:32])C1C=CC=CC=1.C([O-])=O.[NH4+].O>[Pd].CN(C=O)C>[F:30][C:21]1[C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:31][CH3:32])[CH:11]=3)[N:16]=[N:15][CH:14]=2)=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[C:24]([CH3:29])[NH:25]2

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 101374817-Benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxycinnoline

Product 1

HCID 1357497764-(4-Fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnolineYield 75.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxycinnoline (500 mg, 1.17 mmol), (prepared as described in Example 3), ammonium formate (740 mg, 11.7 mmol), 10% palladium on charcoal (100 mg) and water (700 μl) in DMF (10 ml) was stirred for 2 hours at ambient temperature. The mixture was filtered on diatomaceous earth and the filtrate was evaporated under vacuum. The residue was triturated with a mixture of ether and pentane (1/1). The solid was filtered, washed with pentane and dried under vacuum to give 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline (300 mg, quant.).

Workup

  1. filtrationThe mixture was filtered on diatomaceous earth
  2. customthe filtrate was evaporated under vacuum
  3. customThe residue was triturated with a mixture of ether and pentane (1/1)
  4. filtrationThe solid was filtered
  5. washwashed with pentane
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5d267b82c9ca47f09b22589d14a7453b
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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