1-(Bromomethyl)-2-(trifluoromethyl)benzene → HCID 57941490, compound

HRID 1438085Notes

Reaction equation

HRID 1438085 reaction equation
[CH3:1][N:2]1[C:10]2[C@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br>CN(C)C=O>[CH3:1][N:2]1[C:10]2[C@:9]3([CH3:14])[C:11]([CH3:12])([CH3:13])[C@@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[N:3]1[CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=1[C:17]([F:16])([F:26])[F:27]

Participants

4

Reactant 2

HCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 57941342HCID 57941342, compound2×

Product 1

HCID 57941490HCID 57941490, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4R,7S)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 48; 115 mg, 0.55 mmol) and 2-(trifluoromethyl)benzyl bromide (133 mg, 0.55 mmol) in dimethylformamide (5.6 mL) was heated at 100° C. overnight. The solvent was evaporated and the residue was purified on a Biotage chromatography system, eluting with 0-5% methanol/dichloromethane. The resulting clear oil was taken up in dichloromethane, washed with saturated aqueous sodium hydrogen carbonate and water, dried (sodium sulfate), filtered, evaporated, and triturated with ether to give (4R,7S)-1,7,8,8-tetramethyl-2-(2-trifluoromethyl-benzyl)-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (32 mg, 16%) as a white solid. APCI(+)-MS (M+H) 365.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on a Biotage chromatography system
  3. washeluting with 0-5% methanol/dichloromethane
  4. washwashed with saturated aqueous sodium hydrogen carbonate and water
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customtriturated with ether

Sources & evidence

ORD record
ord-283f4e68fdab46fd91260acf78334a91
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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