Sodium hydride → HCID 15486856, compound

HRID 1838339Notes

Reaction equation

HRID 1838339 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:18][C:9]2=[N:10][CH:11]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:13]=[C:8]2[CH:7]=1.[H-].[Na+].Br[CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[Cl-].[NH4+]>CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:18]([CH2:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:9]2=[N:10][CH:11]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:13]=[C:8]2[CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 137636Cyclohexane, (bromomethyl)-HCID 15486854HCID 15486854, compound

Product 1

HCID 15486856HCID 15486856, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-furanyl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (5.5 mg) in N,N-dimethylformamide (0.5 ml), 60% sodium hydride (1.3 mg) was added at 0° C. under nitrogen atmosphere and the mixture was stirred for 30 minutes, followed by addition of bromomethylcyclohexane (7.4 mg), and the reaction mixture was stirred at 15 to 30° C. for 5 hours and at 60° C. for 1 hour. The reaction solution was then poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 4.5 mg of the desired product as a white powder.

Workup

  1. stirringthe reaction mixture was stirred at 15 to 30° C. for 5 hours and at 60° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Sources & evidence

ORD record
ord-c739d9d55154478e89b7b9311761b9a0
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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