Ethyl chloroacetate → HCID 60055729, compound

HRID 1765576Notes

Reaction equation

HRID 1765576 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[CH:10]=2)=[CH:5][C:4]=1[OH:18].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C)C=O>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][O:18][C:4]1[CH:5]=[C:6]([C:9]2[NH:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[CH:10]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH3:31]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 10796Cesium carbonateHCID 22477532HCID 22477532, compound

Product 1

HCID 60055729HCID 60055729, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-phenol [0.5 g, Example 28] in dimethylformamide (10 mL) and cesium carbonate (0.67g) was added ethyl chloroacetate (0.025 g). The reaction mixture was heated at 50° C. overnight. After cooling, the dimethylformamide was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic fraction was dried over sodium sulfate, evaporated and subjected to flash column chromatography on silica eluting with 2.5% methanol in dichloromethane. This product was further triturated with a mixture of ethyl acetate and pentane to give the title compound as a white solid, m.p. 183–184° C. MS: 328 (MH+).

Workup

  1. temperatureAfter cooling
  2. customthe dimethylformamide was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe organic fraction was dried over sodium sulfate
  5. customevaporated
  6. customThis product was further triturated with a mixture of ethyl acetate and pentane

Sources & evidence

ORD record
ord-7e04ceaf99104cb7bc3b2bf318875466
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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