Ethyl chloroacetate → HCID 60055729, compound

HRID 549017Notes

Reaction equation

HRID 549017 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 (0.67 g) 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-d7ff7c92560e40a3aec27e88485ac450
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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