Diisopropylamine → HCID 10287915, compound

HRID 2080569Notes

Reaction equation

HRID 2080569 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[O:15][C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]=1[CH3:19].[F:24][C:25]([F:42])([F:41])[C:26](=[O:40])[CH2:27][C:28]([C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][CH3:39])([CH3:30])[CH3:29]>C1COCC1>[F:42][C:25]([F:24])([F:41])[C:26]([CH2:13][C:14]1[O:15][C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]=1[CH3:19])([OH:40])[CH2:27][C:28]([C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][CH3:39])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 2734646Benzofuran, 2,3-dimethyl-HCID 100849201,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-oneHCID 178418339Butyllithium

Product 1

HCID 10287915HCID 10287915, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium (0.246 mL, 1.6 M in hexanes) was added to a solution of diisopropyl amine (0.055 mL, 0.45 mmol) in anhydrous THF (5 mL) at 0° C. The reaction mixture was cooled to −78° C. and stirred for 15 minutes. A solution of 2,3-dimethylbenzofuran (48 mg, 0.4 mmol) in 2 mL anhydrous THF was added dropwise to this mixture. After the addition, the reaction mixture was stirred for 15 to 30 minutes. 1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one (100 mg, 0.4 mmol) (Example 1) was added as a solution in anhydrous THF (2 mL) in one portion, the cold bath was removed, and the reaction was stirred at room temperature for 12 hours. THF was evaporated under reduced pressure. Water (2 mL) was added to the residue and the mixture was extracted with three 5 mL portions of EtOAc. The extract was dried over magnesium sulfate. After evaporation, the residue was chromatographed on a silica gel column to provide 80 mg of the title compound as an oil.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for 15 to 30 minutes
  3. customthe cold bath was removed
  4. stirringthe reaction was stirred at room temperature for 12 hours
  5. customTHF was evaporated under reduced pressure
  6. additionWater (2 mL) was added to the residue
  7. extractionthe mixture was extracted with three 5 mL portions of EtOAc
  8. dry with materialThe extract was dried over magnesium sulfate
  9. customAfter evaporation
  10. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-e63078c784be4ed0bdcc5c14265bd35a
Source dataset
uspto-grants-2011_04
Patent number
US07932392B2

Reaction notes

Loading…