Triethylamine → 5-((2-chloropyrimidin-4-yl)oxy)-2-methyl-1H-indole

HRID 1396823Notes

Reaction equation

HRID 1396823 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[OH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:19])=[CH:13]2.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([CH3:19])=[CH:13]3)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 833362-methyl-1H-indol-5-ol

Product 1

HCID 598233595-((2-chloropyrimidin-4-yl)oxy)-2-methyl-1H-indoleYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloropyrimidine (1 mmol) and 5-hydroxy-2-methylindole (1 mmol) in 5 ml EtOH was added Et3N (1 mmol). The reaction mixture was refluxed for 5 h. After removal of the solvent in vacuo and addition of H2O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aqueous solution, dried over anhydrous Na2SO4, and concentrated in vacuo. The resulting oil residue was purified by column chromatography to give 5-(2-chloropyrimidin-4-yloxy)-2-methyl-1H-indole in a yield of 75%.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customAfter removal of the solvent
  3. additionin vacuo and addition of H2O
  4. extractionthe mixture was extracted with EtOAc
  5. washwashed with a saturated NaCl aqueous solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting oil residue was purified by column chromatography

Sources & evidence

ORD record
ord-def42d2cc1704c8ca0810b5209374f1d
Source dataset
uspto-grants-2014_12
Patent number
US08901143B2

Reaction notes

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