HCID 67439036, compound → HCID 67438076, compound

HRID 1890265Notes

Reaction equation

HRID 1890265 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[NH:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:12]=1)C1C=CC=CC=1>ClCCl.[Fe](Cl)(Cl)Cl>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:12]=[C:11]([CH2:10][CH2:9][OH:8])[NH:15][N:14]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 67439036HCID 67439036, compound

Product 1

HCID 67438076HCID 67438076, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent2×

Procedure

39.4 g (242 mmol) of iron(III) chloride are initially charged in 200 ml of dichloromethane. At room temperature, a solution of 7.20 g (24.2 mmol) of 5-[2-(benzyloxy)ethyl]-3-(4-fluorophenyl)-1H-pyrazole in 90 ml of dichloromethane is added dropwise. After 20 min, the reaction mixture is washed with 2×100 ml of water. The combined aqueous phases are adjusted to pH 5-6 using sodium bicarbonate and extracted with 2×100 ml of ethyl acetate. The combined organic phases are washed with water, dried over MgSO4 and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 3.40 g (67%) of the desired product; log P(HCOOH): 1.39; 1H-NMR (DMSO-d6): 7.79 (dd, 2H), 7.19 (dd, 2H), 6.47 (s, 1H), 4.79 (t, 1H), 3.65 (m, 2H), 2.76 (t,

Workup

  1. washthe reaction mixture is washed with 2×100 ml of water
  2. extractionextracted with 2×100 ml of ethyl acetate
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over MgSO4
  5. customPurification by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-810d479b485d4732b56b00297b882ff5
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

Loading…