Dimethylformamide → 1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-4-iodo-3,5-dimethyl-1H-pyrazole

HRID 2095640Notes

Reaction equation

HRID 2095640 reaction equation
[CH3:1][C:2]1[C:6]([I:7])=[C:5]([CH3:8])[NH:4][N:3]=1.CC1C=CC(S(O[CH2:20][C@@H:21]2[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].O1CCOCCOCCOCCOCCOCC1.CN(C=O)C>>[CH3:26][C:23]1([CH3:27])[O:22][C@H:21]([CH2:20][N:3]2[C:2]([CH3:1])=[C:6]([I:7])[C:5]([CH3:8])=[N:4]2)[CH2:25][O:24]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 971153,5-Dimethyl-4-iodo-1H-pyrazoleHCID 2723760(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate

Product 1

HCID 670042591-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-4-iodo-3,5-dimethyl-1H-pyrazole

Conditions

Temperature
70 °C

Procedure

A mixture of 3,5-dimethyl-4-iodopyrazole (200.0 mg, 0.9008 mmol), ((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (515.9 mg, 1.802 mmol), K2CO3 (136.9 mg, 0.9909 mmol), 1,4,7,10,13,16-hexaoxacyclooctadecane (23.81 mg, 0.09008 mmol) and DMF (4 mL, 50 mmol) was heated to 70° C. overnight. The material was extracted in EtOAc, and washed with water (3×). The organic layer was dry-loaded onto silica gel for column chromatography, eluting with 20-30% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid.

Workup

  1. extractionThe material was extracted in EtOAc
  2. washwashed with water (3×)
  3. washeluting with 20-30% EtOAc/hexanes
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-c8ef318e0d684e918516f9ce918c20aa
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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