2-Bromopyridine → HCID 10468921, compound

HRID 1376112Notes

Reaction equation

HRID 1376112 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].Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>C(OCC)(=O)C.ClCCl>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[NH: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]

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 732887Ethyl 3-amino-1H-indole-2-carboxylate

Product 1

HCID 10468921HCID 10468921, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Heat a mixture of ethyl 3-aminoindole-2-carboxylate (250 mg, 1.2 mmol) and 2-bromopyridine (1.0 mL, 10 mmol) at 150° C. for 1 h. Cool the reaction and partition between aqueous ammonium chloride and ethyl acetate. Separate the organic layer 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 282(M+H).

Workup

  1. temperatureHeat
  2. temperatureCool
  3. customthe reaction
  4. custompartition between aqueous ammonium chloride and ethyl acetate
  5. customSeparate the organic layer
  6. concentrationconcentrate
  7. customto afford a crude mixture

Sources & evidence

ORD record
ord-add45df1d04a4a32a96147a887d20767
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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