Cyclohexanone → HCID 59252751, compound

HRID 563368Notes

Reaction equation

HRID 563368 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](I)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[C:23]1(=[O:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:23]4([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 592511281-(4-fluorophenyl)-5-iodo-1H-indazoleHCID 178418339Butyllithium

Product 1

HCID 59252751HCID 59252751, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1-(4-Fluorophenyl)-5-iodo-1H-indazole (2.0 g, 5.9 mmol) was dissolved in dry THF (30 mL), cooled to −78° C., and treated with nBuLi (4 mL, 1.6 M in hexanes, 6.5 mmol). After 1 h, cyclohexanone (919 uL, 8.88 mmol) was added all at once and the reaction was allowed to warm to rt. The crude reaction was extracted from water using EtOAc and the combined organic layers were dried with MgSO4, concentrated in vacuo, filtered, and chromatographed on a SiO2 MPLC column using 25% EtOAc in hexanes. Obtained 700 mg (38%) of 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)cyclohexanol. MS found: (M+H)+=311.

Workup

  1. temperatureto warm to rt
  2. customThe crude reaction
  3. extractionwas extracted from water
  4. dry with materialthe combined organic layers were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered
  7. customchromatographed on a SiO2 MPLC column

Sources & evidence

ORD record
ord-5e6b840a01f74806863472f72bf077c9
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

Loading…