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

HRID 2095703Notes

Reaction equation

HRID 2095703 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C1(C)C=CC(S(O[CH2:17][C@H:18]2[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[O:19]2)(=O)=O)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>>[CH3:23][C:20]1([CH3:24])[O:19][C@@H:18]([CH2:17][N:4]2[CH:3]=[C:2]([I:1])[CH:6]=[N:5]2)[CH2:22][O:21]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 6993835(R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate

Product 1

HCID 670044251-{[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methyl}-4-iodo-1H-pyrazole

Conditions

Temperature
100 °C

Procedure

A mixture of 4-iodopyrazole (1.00 g, 5.16 mmol), (R)-(−)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl p-toluenesulfonate (1.624 g, 5.671 mmol), Cs2CO3 (2.52 g, 7.73 mmol) and DMF (8 mL, 100 mmol) was heated to 100° C. for 2 h. The solution was extracted with EtOAc, and washed with water (2×). The organic layer was concentrated in vacuo and purified via column chromatography, eluting with 2-10% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. MS (ES+): m/z=309.00 (100) [MH+]. HPLC: tR=1.32 min (polar—3 min, UPLC-ACQUITY).

Workup

  1. extractionThe solution was extracted with EtOAc
  2. washwashed with water (2×)
  3. concentrationThe organic layer was concentrated in vacuo
  4. custompurified via column chromatography
  5. washeluting with 2-10% EtOAc/hexanes
  6. additionThe fractions containing the pure product
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-1277b257bca549d7a2175c9a915407fc
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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