Potassium Carbonate → 1-(1,4-Dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole

HRID 1926343Notes

Reaction equation

HRID 1926343 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[I:22][C:23]1[CH:24]=[N:25][NH:26][CH:27]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.O>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([N:25]3[CH:24]=[C:23]([I:22])[CH:27]=[N:26]3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 770224-IodopyrazoleHCID 5674891,4-Dioxaspiro[4.5]decan-8-ol, 8-(4-methylbenzenesulfonate)

Product 1

HCID 595411251-(1,4-Dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of toluene-4-sulfonic acid 1,4-dioxaspiro[4.5]dec-8-yl ester (2.0 g, 6.4 mmol; prepared according to U.S. Pat. No. 4,360,531 example I.B), 4-iodopyrazole (1.36 g, 7.01 mmol), K2CO3 (1.06 g, 7.7 mmol), 18-crown-6 (0.2 g, 0.7 mmol) in DMF (5 mL) was heated under nitrogen at 50° C. for 16 h. Water (50 mL) was added, and the reaction mixture was extracted with EtOAc (3×40 mL). The EtOAc extracts were washed with water (30 mL), dried over Na2SO4, filtered, and concentrated at reduced pressure. The crude material was purified by column chromatography on silica gel using EtOAc/CH2Cl2 (1:9) to give the title compound. 1H NMR (CDCl3, 300 MHz): δ=1.66-2.17 (m, 8H), 3.97 (s, 4H), 4.17-4.23 (m, 1H), 7.27 (d, J=3.3 Hz, 1H), 7.48 (d, J=3.3 Hz, 1H).

Workup

  1. customprepared
  2. customwas heated under nitrogen at 50° C. for 16 h
  3. extractionthe reaction mixture was extracted with EtOAc (3×40 mL)
  4. washThe EtOAc extracts were washed with water (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customThe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cd6286ceaa954bfda3b22c833a035768
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

Loading…