Isopropyl iodide → HCID 67261810, compound

HRID 2359054Notes

Reaction equation

HRID 2359054 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([C:9]3[S:10][C:11]([Cl:14])=[CH:12][CH:13]=3)[C:5]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:3][CH2:2]1.I[CH:22]([CH3:24])[CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[CH:1]1([C:4]2[N:8]([CH:22]([CH3:24])[CH3:23])[N:7]=[C:6]([C:9]3[S:10][C:11]([Cl:14])=[CH:12][CH:13]=3)[C:5]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:3][CH2:2]1.[CH:1]1([C:4]2[C:5]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:6]([C:9]3[S:10][C:11]([Cl:14])=[CH:12][CH:13]=3)[N:7]([CH:22]([CH3:24])[CH3:23])[N:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 672602794-[3-(5-chloro-2-thienyl)-5-cyclopropyl-1H-pyrazol-4-yl]pyridine

Product 2

HCID 67260794HCID 67260794, compoundYield 26%HCID 67261810HCID 67261810, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[5-cyclopropyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (1 eq, 0.32 mmol) in 2 mL N,N-dimethylformamide were added 2-iodopropane (1.5 eq, 0.48 mmol) and cesium carbonate (2 eq, 0.64 mmol). The reaction mixture was stirred overnight at room temperature, diluted with water and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (heptane:ethyl acetate 5:1 to 1:1) to afford 28.8 mg of 4-[5-cyclopropyl-1-isopropyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (26% yield) and 30.2 mg of 4-[3-cyclopropyl-1-isopropyl-5-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (28% yield).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (heptane:ethyl acetate 5:1 to 1:1)

Sources & evidence

ORD record
ord-a7fdf578ec874c708559f9073742f4b1
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

Loading…