Ethyl Acetate → HCID 10107810, compound

HRID 1376113Notes

Reaction equation

HRID 1376113 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl[C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[Cl-].[NH4+].C(OCC)(=O)C>C(OCC)(=O)C.ClCCl>[CH2:14]([O:13][C:11]([C:3]1[NH:4][C:5]2[C:10]([C:2]=1[NH:1][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:12])[CH3:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 744042-ChloropyrimidineHCID 732887Ethyl 3-amino-1H-indole-2-carboxylate

Product 1

HCID 10107810HCID 10107810, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Heat a mixture of ethyl 3-aminoindole-2-carboxylate (204 mg, 1.0 mmol) and 2-chloropyrimidine (1.2 g, 10.5 mmol) at 100° C. for 16 h. Cool the reaction and add aqueous ammonium chloride and ethyl acetate. Filter off excess 2-chloropyrimidine, separate the organic layer, dry with MgSO4, filter and concentrate to afford a crude mixture. Flash chromatograph the mixture on silica gel eluting with 25% ethyl acetate/dichloromethane to afford 50 mg of the title compound: MS 283 (M+H), TLC (silica gel, 25% ethyl acetate/dichloromethane) Rf=0.44.

Workup

  1. temperatureHeat
  2. temperatureCool
  3. customthe reaction
  4. filtrationFilter off excess 2-chloropyrimidine
  5. customseparate the organic layer
  6. dry with materialdry with MgSO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto afford a crude mixture

Sources & evidence

ORD record
ord-a547485a581749eb9f64f5b4bf0afb1f
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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