HCID 22612197, compound → HCID 22612328, compound

HRID 844054Notes

Reaction equation

HRID 844054 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][C:14]2[C:15]([O:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:28][Li]>O1CCCC1>[F:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][C:15]2[C:14]([NH:13][C:11](=[O:12])[CH2:10][C:7]3[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:28])[CH3:2])=[CH:9][CH:8]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 22612197HCID 22612197, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 22612328HCID 22612328, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a 2-(4-Acetyl-phenyl)-N-[2-(4-fluoro-phenoxy)-pyridin-3-yl]-acetamide (0.270 grams, 0.741 mmole) in tetrahydrofuran (15 ml) at −78° C. 1.0 M methyl lithium in tetrahydrofuran (1.63 ml, 1.63 mmole) was added via syringe and stirred at −78° C. for 75 minutes. Another 0.8 ml methyl lithium was added and the mixture was warmed to 0° C. for 10 minutes and cooled to −78° C. The mixture was quenched with water, allowed to warm to room temperature and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated to a white solid which was purified by chromatography on silica eluting with 2% methanol/methylene chloride to give a white solid. Recrystalization from ethyl acetate/hexane gave a solid (0.032 g). M.P. 135-137° C.; Anal. calcd. for C22H21N2O3F: C, 69.46; H, 5.56; N, 7.36. Found: C, 69.46; H, 5.92; N, 7.73.

Workup

  1. customat −78° C
  2. temperaturethe mixture was warmed to 0° C. for 10 minutes
  3. temperaturecooled to −78° C
  4. customThe mixture was quenched with water
  5. temperatureto warm to room temperature
  6. extractionextracted with ethyl acetate
  7. washThe combined organics were washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to a white solid which
  11. customwas purified by chromatography on silica eluting with 2% methanol/methylene chloride
  12. customto give a white solid
  13. customRecrystalization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3058cd7694994df1bed585a8e7d07261
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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