HCID 21069850, compound → HCID 21069796, compound

HRID 1726576Notes

Reaction equation

HRID 1726576 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2([C:12]([F:15])([F:14])[F:13])[N:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CN(C)C=O>[F:13][C:12]([F:15])([F:14])[C:9]1([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH2:2][N:20]2[C:16](=[O:26])[C:17]3[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:19]2=[O:21])[NH:11][NH:10]1

Participants

4

Reactant 2

HCID 21069850HCID 21069850, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 21069796HCID 21069796, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of intermediate 64, 3-(3-bromomethyl-phenyl)-3-trifluoromethyl-3H-diazirine, (140 mg, 0.5 mmol) and potassium phthalimide (95 mg, 0.5 mmol) in dimethylformamide (1.5 mL) was stirred at room temperature for 3 hrs. Dimethylformamide was removed in vacuo. The residue was extracted with CH2Cl2, washed with water, then dried (Na2SO4), filtered, and concentrated. The resulting residue was purified by column chromatography (SiO2, 1:1 CH2Cl2/pentane) to provide 140 mg (Yield 82%) of the title compound as a solid; 1H NMR (300 MHz, CDCl3) δ ppm: 4.80 (2H, s) 7.09-7.21 (2H, m) 7.32 (1H, t, J=7.9 Hz) 7.41-7.49 (2H, m) 7.66-7.71 (2H, m) 7.81-7.85 (2H, m); LC/MS m/z 346 (M+H).

Workup

  1. customDimethylformamide was removed in vacuo
  2. extractionThe residue was extracted with CH2Cl2
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography (SiO2, 1:1 CH2Cl2/pentane)

Sources & evidence

ORD record
ord-49956b4d7b4b473f914feebe045dc567
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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