Triethylamine → HCID 23363004, compound

HRID 1608628Notes

Reaction equation

HRID 1608628 reaction equation
[SH:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][N:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:23].C(N(CC)CC)C>C(O)C>[C:15]1(=[O:23])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][N:14]1[CH2:13][CH2:12][S:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 146241772-[2-(Bromo)ethyl]isoindolin-1-oneHCID 178418687HCID 178418687, compound

Product 1

HCID 23363004HCID 23363004, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (150 mg, 1 mmole) and 2-[2-(bromo)ethyl]isoindolin-1-one (240 mg, 1 mmole) in ethanol (15 ml) was added triethylamine (0.21 ml, 1.5 mmoles) and the mixture was stirred at room temperature for 12 hours and heated at reflux for 2 hours. After the solvent was distilled off, chloroform was added to the residue which was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography [eluent: ethyl acetate/ethanol (15:1)] to obtain 238 mg of the desired product (77.0%, light brown solid).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. distillationAfter the solvent was distilled off
  4. additionchloroform was added to the residue which
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe residue was purified by column chromatography [eluent: ethyl acetate/ethanol (15:1)]

Sources & evidence

ORD record
ord-224099831c2045579052f3d927f2bd07
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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