Dimethylformamide → HCID 69331778, compound

HRID 351247Notes

Reaction equation

HRID 351247 reaction equation
O[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([C:21]([F:24])([F:23])[F:22])[C:9]=2[CH3:25])[CH:7]=1.Br[CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].[H-].[Na+].CN(C=[O:43])C>>[Si:30]([O:29][CH2:28][CH2:27][O:43][C:3]1[CH:2]=[CH:7][C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([C:21]([F:23])([F:22])[F:24])[C:9]=2[CH3:25])=[CH:5][CH:4]=1)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 21091019HCID 21091019, compound

Product 1

HCID 69331778HCID 69331778, compoundYield 73%

Procedure

To a solution of 5-(hydroxyl)phenyl-1-(4-methoxyphenyl)-4-methyl-3-(trifluoromethyl)-1H-pyrazole (5.0 g) and 2-bromoethoxy-tert-butyldimethylsilane (6.87 g) in DMF (100 ml) was added portionwise NaH (919 mg, 50% in oil) at room temperature. The reacion mixture was stirred overnight. The reaction mixture was quenched with water. Aqueouslayer was extracted twice with EtOAc. Combined organic layer was washed twice with water, and brine. Dried, filtered and evaporated under reduced pressure to give 5.29 g (73%) of 5-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}-ethoxy)phenyl]-1-(4-methoxyphenyl)-4-methyl-3-(trifluoromethyl)-1-H-pyrazole.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionAqueouslayer was extracted twice with EtOAc
  3. washCombined organic layer was washed twice with water, and brine
  4. customDried
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-62db0a573bd4400a8d5874b241a19dec
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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