Dimethylformamide → methyl 3-(4-iodo-1H-pyrazol-1-yl)propanoate

HRID 1926355Notes

Reaction equation

HRID 1926355 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.Cl[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]>CCOC(C)=O>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 22321Methyl 3-chloropropionateHCID 770224-Iodopyrazole

Product 1

HCID 64435500methyl 3-(4-iodo-1H-pyrazol-1-yl)propanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-iodopyrazole (1.000 g, 5.155 mmol), Cs2CO3 (2.016 g, 6.186 mmol), and DMF (20 mL, 0.2 mol) was added methyl 3-chloropropanoate (758.1 mg, 6.186 mmol) at 0° C. The reaction was heated to 50° C. for 1 h. The material was transferred to a separatory funnel, diluted with EtOAc, and washed with water several times to remove DMF. The organic layer was dry-loaded onto silica gel, and column chromatography was used for purification, eluting with 3:1 Hexanes/EtOAc, affording the title compound as a clear liquid. MS (ES+): m/z=280.95 (100) [MH+]. HPLC: tR=2.91 min (ZQ3, polar—5 min).

Workup

  1. customThe material was transferred to a separatory funnel
  2. washwashed with water several times
  3. customto remove DMF
  4. customwas used for purification
  5. washeluting with 3:1 Hexanes/EtOAc

Sources & evidence

ORD record
ord-013d4ab7a0e647519da4711fb98ef0af
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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