Potassium Carbonate → HCID 86590189, compound

HRID 2180128Notes

Reaction equation

HRID 2180128 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18](O)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[N:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:25])[NH:6]2.C(OC(N1CCC(COS(C2C=CC(C)=CC=2)(=O)=O)CC1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[N:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:25])[NH:6]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidineHCID 1357497764-(4-Fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline

Product 1

HCID 86590189HCID 86590189, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen a mixture of 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxycinnoline (150 mg, 0.44 mmol), (prepared as described in Example 4), 1-(tert-butoxycarbonyl)-4-(4-methylphenylsulfonyloxymethyl)piperidine (196 mg, 0.53 mmol) and potassium carbonate (122 mg, 0.88 mmol) in DMF (6 ml) was stirred at 100° C. for 2.5 hours. The mixture was filtered, and filtrate was evaporated under vacuum. The residue was purified by column chromatography eluting with methylene chloride followed by methylene chloride/methanol (99/1 and 95/5). The fractions containing the expected product were combined and evaporated. The residue was triturated with a mixture of pentane/ether (1/1) and the solid was filtered, washed with pentane and dried under vacuum to give 7-(1-(tert-butoxycarbonyl)piperidin-4-yl)methoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxycinnoline (100 mg, 42%).

Workup

  1. filtrationThe mixture was filtered
  2. customfiltrate was evaporated under vacuum
  3. customThe residue was purified by column chromatography
  4. washeluting with methylene chloride
  5. additionThe fractions containing the expected product
  6. customevaporated
  7. customThe residue was triturated with a mixture of pentane/ether (1/1)
  8. filtrationthe solid was filtered
  9. washwashed with pentane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-1c1d425037bf494aa8517c536a0dcc81
Source dataset
uspto-grants-2005_05
Patent number
US06887874B2

Reaction notes

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