Cesium carbonate → HCID 59712239, compound

HRID 2222413Notes

Reaction equation

HRID 2222413 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:16][C:17]1[C:25]([OH:26])=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[C:20]([CH3:27])[NH:21]2.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:26][C:25]1[C:17]([F:16])=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20]([CH3:27])=[CH:19]2)#[N:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 22646547HCID 22646547, compound

Product 1

HCID 59712239HCID 59712239, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 4-chloro-6-cyano-7-methoxyquinoline (200 mg, 0.91 mmol), (prepared as described for the starting material in Example 1), 4-fluoro-5-hydroxy-2-methylindole (181 mg, 1.1 mmol), (prepared as described for the starting material in Example 11), and cesium carbonate (444 mg, 1.36 mmol) in DMF (6 ml) was heated at 95° C. for 2.5 hours. After cooling, the mixture was filtered, the filtrate was evaporated under vacuum and the residue was purified by column chromatography eluting with methylene chloride, followed by methanol/ethyl acetate/methylene chloride (2/10/88 followed by 5/15/80) to give 6-cyano-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinoline (111 mg, 35%).

Workup

  1. custom(prepared
  2. custom(prepared
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated under vacuum
  6. customthe residue was purified by column chromatography
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-ec3d4961d8734d108f188170f871e810
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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