Sodium hydride → HCID 86698175, compound

HRID 623928Notes

Reaction equation

HRID 623928 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:14]=2)=[CH:6][N:5]=1.[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl.[Cl-].[NH4+]>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:27])([CH3:26])[CH3:19])[CH:13]=[C:12]([C:15]([F:18])([F:16])[F:17])[N:11]=2)=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 86698184HCID 86698184, compound

Product 1

HCID 86698175HCID 86698175, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride (2.62 g) was added to a solution of 2-bromo-5-[5-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (13.65 g) dissolved in N,N-dimethylformamide (150 mL) under nitrogen atmosphere and under ice-cooling, and the mixture was stirred for 30 minutes. To the mixture was added 2-(trimethylsilyl)ethoxymethyl chloride (12.4 mL) under ice-cooling, and the mixture was stirred overnight while the temperature of the mixture was gradually raised to room temperature. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the aqueous layer at this time was extracted with ethyl acetate. The organic layers were combined and dried, and the residue obtained by concentrating the reaction mixture under reduced pressure was purified by silica gel column chromatography (n-hexane:ethyl acetate) to obtain 2-bromo-5-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]-methyl}-1H-imidazol-2-yl]pyridine (9.42 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred overnight while the temperature of the mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. extractionthe aqueous layer at this time was extracted with ethyl acetate
  7. customdried
  8. customthe residue obtained
  9. concentrationby concentrating the reaction mixture under reduced pressure
  10. customwas purified by silica gel column chromatography (n-hexane:ethyl acetate)

Sources & evidence

ORD record
ord-ef3765d27c8d40d897af1ed239b43c4f
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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