Methanol → HCID 66997594, compound

HRID 559167Notes

Reaction equation

HRID 559167 reaction equation
[H-].[Na+].CN([CH:6]=[O:7])C.CO.[Cl:10][C:11]1[CH:16]=[C:15](F)[CH:14]=[CH:13][C:12]=1[C:18]1[C:31](=[O:32])[N:30]([CH3:33])[C:21]2[N:22]([CH3:29])[C:23]3[C:28]([C:20]=2[CH:19]=1)=[CH:27][CH:26]=[CH:25][CH:24]=3>O>[Cl:10][C:11]1[CH:16]=[C:15]([O:7][CH3:6])[CH:14]=[CH:13][C:12]=1[C:18]1[C:31](=[O:32])[N:30]([CH3:33])[C:21]2[N:22]([CH3:29])[C:23]3[C:28]([C:20]=2[CH:19]=1)=[CH:27][CH:26]=[CH:25][CH:24]=3

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66998084HCID 66998084, compound

Product 1

HCID 66997594HCID 66997594, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3.25 g (81.1 mmol) of 60% NaH are added to 300 ml of DMF and 9.6 ml of MeOH. The mixture is left to stir for 5 minutes, and then 9.22 g (27.0 mmol) of compound A 3-(2-chloro-4-fluorophenyl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one are added. The mixture is stirred at ambient temperature and then, as soon as no more gas is being given off, is heated at 80° C. for 16 h. The reaction medium is left to cool and poured into H2O, the yellow precipitate is filtered off and washed with H2O, the residue is taken up in MeOH and the product is concentrated to dryness.

Workup

  1. waitThe mixture is left
  2. stirringThe mixture is stirred at ambient temperature
  3. waitThe reaction medium is left
  4. temperatureto cool
  5. filtrationthe yellow precipitate is filtered off
  6. washwashed with H2O
  7. concentrationthe product is concentrated to dryness

Sources & evidence

ORD record
ord-29f1b767d4344d3e85655a48de5eaabe
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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