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

HRID 1926351Notes

Reaction equation

HRID 1926351 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.[CH3:18][O:19][C:20](=[O:23])[CH2:21]Cl>CCOC(C)=O>[CH3:18][O:19][C:20](=[O:23])[CH2:21][N:4]1[CH:3]=[C:2]([I:1])[CH:6]=[N:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7295Methyl chloroacetateHCID 10796Cesium carbonateHCID 770224-Iodopyrazole

Product 1

HCID 51072288methyl (4-iodo-1H-pyrazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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 chloroacetic acid methyl ester (0.5440 mL, 6.186 mol) at 0° C. The reaction was allowed to stir for 1 h at rt. 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 to purify, eluting with 3:1 Hexanes/EtOAc, affording the title compound as a clear liquid. 1H NMR (400 MHz, CDCl3): δ=3.79 (s, 3H), 4.93 (s, 2H), 7.54 (s, 1H), 7.57 (s, 1H). MS (ES+): m/z=266.95 (100) [MH+]. HPLC: tR=2.73 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. customto purify
  5. washeluting with 3:1 Hexanes/EtOAc

Sources & evidence

ORD record
ord-b6d1b8c8307c4c958b6a4b64cc4690ff
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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