Methyl iodide → 2-(5-bromo-pyridin-3-yl)-1-methyl-1H-indole

HRID 712605Notes

Reaction equation

HRID 712605 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=[N:8][CH:9]=1.[CH3:19]I>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]([C:10]2[N:11]([CH3:19])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 582156752-(5-bromopyridin-3-yl)-1H-indole

Product 1

HCID 1022297482-(5-bromo-pyridin-3-yl)-1-methyl-1H-indoleYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% NaH (84 mg, 2.1 mmol) is added to a solution of 2-(5-bromo-pyridin-3-yl)-1H-indole (192 mg, 0.70 mmol) in THF (20 mL) and the temperature is kept below 0° C. After the addition, the mixture is stirred at room temperature for 30 min. MeI (125 mg, 0.88 mmol) is added to the mixture at 0° C. and the mixture is stirred at room temperature for 3 hrs. Then the solvent is removed and the residue is dissolved in EtOAc and washed with water. The organic layer is separated, dried and concentrated. The crude product is purified by flash column chromatography to give 173 mg of 2-(5-bromo-pyridin-3-yl)-1-methyl-1H-indole.

Workup

  1. customis kept below 0° C
  2. additionAfter the addition
  3. stirringthe mixture is stirred at room temperature for 3 hrs
  4. customThen the solvent is removed
  5. dissolutionthe residue is dissolved in EtOAc
  6. washwashed with water
  7. customThe organic layer is separated
  8. customdried
  9. concentrationconcentrated
  10. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-5e57dc7cbab7463c8815c9c2df417d02
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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