Cesium carbonate → HCID 58913548, compound

HRID 1296936Notes

Reaction equation

HRID 1296936 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[C:28]([I:29])=[CH:27][NH:26][N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:36][Si:37]([CH3:44])([CH3:43])[CH2:38][CH2:39][O:40][CH2:41]Cl>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([Cl:23])=[CH:11][C:10]=1[C:24]1[C:28]([I:29])=[CH:27][N:26]([CH2:41][O:40][CH2:39][CH2:38][Si:37]([CH3:44])([CH3:43])[CH3:36])[N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178477918HCID 178477918, compound

Product 1

HCID 58913548HCID 58913548, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(2,4-bis-benzyloxy-5-chloro-phenyl)-4-iodo-1H-pyrazole (4.46 g, 8.63 mmol) and caesium carbonate (8.43 g, 25.88 mmol) in DMF (50 ml) was added 2-(trimethylsilyl)ethoxymethyl chloride (2.29 ml, 12.94 mmol). The mixture was stirred at room temperature overnight before being partitioned between water and DCM. The organics were then washed with brine and water and concentrated in vacuo to give a yellow oil which was purified by column chromatography using hexanes and ethyl acetate as eluent, yielding 3-(2,4-bis-benzyloxy-5-chloro-phenyl)-4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole as a clear colourless oil (4.44 g, 80%).

Workup

  1. custombefore being partitioned between water and DCM
  2. washThe organics were then washed with brine and water
  3. concentrationconcentrated in vacuo
  4. customto give a yellow oil which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-54743caf339d45d6a13071f79a0a3ed0
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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