Tetrahydrofuran → HCID 9863870, compound

HRID 365484Notes

Reaction equation

HRID 365484 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([CH2:28][CH3:29])=[N:17][N:18]3[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:14][CH:13]=2)=[CH:8][CH2:7]1)=[O:5])C.O1CCCC1.[OH-].[Na+]>CO>[CH2:28]([C:16]1[C:15]2[C:19](=[CH:20][C:12]([C:9]3[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH:8]=3)=[CH:13][CH:14]=2)[N:18]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[N:17]=1)[CH3:29]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 9886817HCID 9886817, compound

Product 1

HCID 9863870HCID 9863870, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1.13 g (2.87 mmol) of 4-(3-ethyl-1-(4-fluorophenyl)-1H-indazol-6-yl)-cyclohex-3-ene-carboxylic acid ethyl ester dissolved in 50 mL of methanol and 15 mL of tetrahydrofuran was added 8.62 mL (8.61 mmol) of 1 N sodium hydroxide and reaction mixture heated to reflux for 3 hr. After 3 hr, the reaction mixture was concentrated on a rotary evaporator, diluted with 200 mL of H2O, acidified to pH 1 with 1N HCl and extracted 2×200 mL ethyl acetate. The organic extracts were combined, washed with water, brine and dried over Na2SO4. Filtration, concentration and drying gave crude product. Recrystallization from ethyl acetate/hexane gave 0.31 grams of white crystalline product. mp=214-216° C.; MS, m/z 365 (M+H+, base).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hr
  3. concentrationthe reaction mixture was concentrated on a rotary evaporator
  4. additiondiluted with 200 mL of H2O
  5. extractionextracted 2×200 mL ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationFiltration, concentration
  9. customdrying
  10. customgave crude product
  11. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-15453c89f7394c1e956564e939559d79
Source dataset
uspto-grants-2000_10
Patent number
US06127398

Reaction notes

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