Sodium hydride → HCID 9951280, compound

HRID 1814066Notes

Reaction equation

HRID 1814066 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]3[N:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:11][C:8]2=[N:9][CH:10]=1)(=[O:4])=[O:3].[H-].[Na+].[CH:22]1([CH2:28]Br)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH:22]1([CH2:28][N:11]2[C:8]3=[N:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=[C:7]3[CH:13]=[C:12]2[C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-3×HCID 516892Sodium BicarbonateHCID 15486862HCID 15486862, compound

Product 1

HCID 9951280HCID 9951280, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-methanesulfonyl-2-(2-pyrimidinyl)-1H-pyrrolo[2,3-b]pyridine (150 mg) in N,N-dimethylformamide (5.5 ml), 60% sodium hydride (32.8 mg) was added at 0° C. under nitrogen atmosphere and the mixture was stirred at the same temperature for 30 minutes. Subsequently, to the mixture was added cyclohexylmethyl bromide (154 mg) at 0° C. and the mixture was stirred at 60° C. for 2 hours, followed by addition of cyclohexylmethyl bromide (77 mg) and stirring of the mixture at the same temperature for 1 hour. Further, to the mixture was added cyclohexylmethyl bromide (77 mg) and the mixture was stirred at 60° C. for 15 hours. Subsequently, the reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform. The organic layer was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (methanol:chloroform=1:20) and further recrystallized (chloroform/hexane) to obtain 109 mg of the desired product as a white needle-like crystal.

Workup

  1. additionwas added at 0° C. under nitrogen atmosphere
  2. stirringthe mixture was stirred at 60° C. for 2 hours
  3. stirringstirring of the mixture at the same temperature for 1 hour
  4. stirringthe mixture was stirred at 60° C. for 15 hours
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with a saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was separated
  11. customfurther recrystallized (chloroform/hexane)

Sources & evidence

ORD record
ord-92eea213553b421a9e9444fa6df23a9b
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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