Dimethylformamide → HCID 59593351, compound

HRID 2387270Notes

Reaction equation

HRID 2387270 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.C([Li])(C)(C)C.CN(C)[CH:27]=[O:28]>O1CCCC1>[F:17][C:16]([F:19])([F:18])[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:5]2[N:6]=[CH:7][C:2]([CH:27]=[O:28])=[CH:3][CH:4]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 59593326HCID 59593326, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59593351HCID 59593351, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (5-bromo-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-amine (21, 3.55 g, 0.0107 mol) in tetrahydrofuran (150 mL), tert-butyllithium (13.2 mL, 1.70 M in pentane, 0.0224 mol) was added slowly under an atmosphere of nitrogen at −78° C. over 10 minutes. The reaction mixture was stirred at −78° C. for 90 minutes. N,N-Dimethylformamide (2.2 mL, 0.028 mol) was added slowly into the reaction mixture. The reaction mixture was stirred at −78° C. for 2 hours, then allowed to warm to room temperature. After stirring at room temperature for 2 hours, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic phase was washed with saturated sodium bicarbonate, brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a light yellow solid (22, 1.67 g, 56%).

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
  2. temperatureto warm to room temperature
  3. stirringAfter stirring at room temperature for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with saturated sodium bicarbonate, brine
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of solvent
  8. customthe residue was purified by silica gel column chromatography
  9. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-5ee8acdb9a884596b732e3593def6033
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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