Cesium carbonate → HCID 11846907, compound

HRID 1172839Notes

Reaction equation

HRID 1172839 reaction equation
[Cl:1][C:2]1[C:27]([OH:28])=[CH:26][C:5]2[C:6]([C:9]3[C:10]([CH2:23][CH2:24][CH3:25])=[N:11][CH:12]=[CH:13][C:14]=3OC3C=CC(Cl)=CC=3)=[N:7][O:8][C:4]=2[CH:3]=1.Br[CH2:30][C:31]([O:33]C)=[O:32].[C:35](=[O:38])([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:27]([O:28][CH2:30][C:31]([OH:33])=[O:32])=[CH:26][C:5]2[C:6]([C:9]3[C:10]([CH2:23][CH2:24][CH3:25])=[N:11][C:12]([O:38][C:35]4[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=4)=[CH:13][CH:14]=3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 68695399HCID 68695399, compound

Product 1

HCID 11846907HCID 11846907, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the phenol from Step 10 (0.42 g, 1.0 mmol), methyl bromoacetate (0.23 g, 1.5 mmol) and cesium carbonate (0.49 g, 1.5 mmol) in DMF (10 mL) was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water and concentrated. The residue was taken up in methanol (10 mL) and treated with 2 NNaOH (1.5 mL) for 1 h. The mixture was acidified with acetic acid (1 mL) and concentrated. The residue was purified by preparative HPLC on a RP-C18 column using 10-100% acetonitrile in water gradient solvent system modified with 0.1% acetic acid to give the title compound as a white solid.

Workup

  1. washwashed with water
  2. concentrationconcentrated
  3. additiontreated with 2 NNaOH (1.5 mL) for 1 h
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC on a RP-C18 column

Sources & evidence

ORD record
ord-3e45fc6024c841af93217962e528115c
Source dataset
uspto-grants-2010_11
Patent number
US07834036B2

Reaction notes

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