Dimethylformamide → HCID 59593351, compound

HRID 1024200Notes

Reaction equation

HRID 1024200 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 (17, 3.55 g, 0.0107 mol, commercially available, or prepared as described in Example 10) in tetrahydrofuran (150 mL) was added tert-butyllithium (13.2 mL, 1.70M in pentane, 0.0224 mol) 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 (18, 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-f2895b9659fc49fbab3a5b2328a80b1d
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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