Cesium carbonate → HCID 22282037, compound

HRID 1062801Notes

Reaction equation

HRID 1062801 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([OH:14])[C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:28]([O:31][CH2:32][CH2:33]Br)(=[O:30])[CH3:29]>CN(C)C=O>[C:28]([O:31][CH2:32][CH2:33][O:14][C:4]1[C:3]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[C:2]([NH2:1])[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:5]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178423916HCID 178423916, compound

Product 1

HCID 22282037HCID 22282037, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of 5-amino-1-benzyl-4-(4-methylphenyl)-1H-pyrazol-3-ol (Preparation 42) (2.4 g) and cesium carbonate (8.4 g) in dimethylformamide (30 ml) under nitrogen at room temperature was added 2-bromoethyl acetate (1.44 g) and the reaction mixture stirred overnight. The reaction was quenched with 2M hydrochloric acid (100 ml) and extracted into ethyl acetate (2×100 ml). The two combined organic extracts were further washed with water (2×100 ml), then dried (MgSO4) and the solvent removed under reduced pressure to give the crude material. This was purified using the Biotage™ Flash 40 system (90 g Silica) with a gradient elution of hexane 75% to 30%) and ethyl acetate (25% to 70%) to yield the title product as a brown oil.(1.75 g, ca. 60%)

Workup

  1. customThe reaction was quenched with 2M hydrochloric acid (100 ml)
  2. extractionextracted into ethyl acetate (2×100 ml)
  3. washThe two combined organic extracts were further washed with water (2×100 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. customto give the crude material
  7. customThis was purified
  8. washwith a gradient elution of hexane 75% to 30%) and ethyl acetate (25% to 70%)

Sources & evidence

ORD record
ord-ffc7b6c88801458fb32b6498a26ea997
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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