Sodium hydride → N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-(2-chloro-pyridin-4-yloxy)-4-methyl-benzamide

HRID 1028429Notes

Reaction equation

HRID 1028429 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:10]([O:24][CH3:25])=[C:11]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([OH:22])[CH:16]=2)[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[H][H].[Cl:33][C:34]1[CH:39]=[C:38](I)[CH:37]=[CH:36][N:35]=1>CN(C)C=O>[C:3]([C:7]1[CH:8]=[C:9]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:10]([O:24][CH3:25])=[C:11]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][C:38]3[CH:37]=[CH:36][N:35]=[C:34]([Cl:33])[CH:39]=3)[CH:16]=2)[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 15165112-Chloro-4-iodopyridineHCID 67217566N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 86664520N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-(2-chloro-pyridin-4-yloxy)-4-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

545 mg sodium hydride (60% in mineral oil) are added to 2.77 g N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamide in 15 ml N,N-dimethylformamide under an argon atmosphere and while cooling with an ice bath, and the reaction mixture is stirred at ambient temperature until no further hydrogen development can be detected. Then 1.63 g 2-chloro-4-iodopyridine are added, and the reaction mixture is stirred overnight at 110° C. After cooling to ambient temperature the solvent is distilled off using the rotary evaporator. The flask residue is taken up in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried on magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with petroleum ether/ethyl acetate (80:20→30:70) as eluant. The product is stirred with diethyl ether, suction filtered and dried.

Workup

  1. temperaturewhile cooling with an ice bath
  2. temperatureAfter cooling to ambient temperature the solvent
  3. distillationis distilled off
  4. customthe rotary evaporator
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  6. customdried on magnesium sulphate
  7. customevaporated down
  8. customThe flask residue is chromatographed through a silica gel column with petroleum ether/ethyl acetate (80:20→30:70) as eluant
  9. stirringThe product is stirred with diethyl ether, suction
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-75c5fbf7167c4af28be6465965ebe07d
Source dataset
uspto-grants-2014_05
Patent number
US08735579B2

Reaction notes

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