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

HRID 1947907Notes

Reaction equation

HRID 1947907 reaction equation
CC1C=CC(S(O[CH:12]2[CH2:21][CH2:20][C:15]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:14][CH2:13]2)(=O)=O)=CC=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:16]1[C:15]2([CH2:14][CH2:13][CH:12]([N:25]3[CH:24]=[C:23]([I:22])[CH:27]=[N:26]3)[CH2:21][CH2:20]2)[O:19][CH2:18][CH2:17]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 1,4-dioxaspiro[4.5]dec-8-yl 4-methylbenzenesulfonate (prepared according to U.S. Pat. No. 4,360,531) (2.0 g, 6.4 mmol), 4-iodopyrazole (1.36 g, 7.0 mmol), K2CO3 (1.06 g, 7.7 mmol), and 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 to the reaction mixture, which was then extracted with EtOAc (3×40 mL). The combined EtOAc extracts were washed with water (30 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel using EtOAc/CH2Cl2 (1:9) to give the title compound. 1H NMR (CDCl3, 400 MHz): δ =1.67-1.76 (m, 2H), 1.84-1.91 (m, 2H), 1.99-2.17 (m, 4H), 3.95-3.99 (m, 4H), 4.18-4.27 (m, 1H). MS (ES+): m/z=334.96 (100) [MH+]. HPLC: tR=3.26 min (polar—5 min, ZQ3).

Workup

  1. customprepared
  2. extractionwas then extracted with EtOAc (3×40 mL)
  3. washThe combined EtOAc extracts were washed with water (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3407aa531c144ced9f7d91d9cc3dea63
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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