Methyl iodide → 3-(2,5-Dichloropyrimidin-4-yl)-1-methyl-1H-indole

HRID 1256019Notes

Reaction equation

HRID 1256019 reaction equation
[H-].[Na+].I[CH3:4].[Cl:5][C:6]1[N:11]=[C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[C:9]([Cl:21])=[CH:8][N:7]=1>C1COCC1>[Cl:5][C:6]1[N:11]=[C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH3:4])[CH:13]=2)[C:9]([Cl:21])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 566553763-(2,5-Dichloropyrimidin-4-yl)-1H-indole2×

Product 1

HCID 580714413-(2,5-Dichloropyrimidin-4-yl)-1-methyl-1H-indoleYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.136 g, 3.41 mmol) and iodomethane (0.533 ml, 8.52 mmol) were added to a flask charged with 3-(2,5-dichloropyrimidin-4-yl)-1H-indole (INTERMEDIATE 2) (0.750 g, 2.84 mmol) and THF (18.40 ml). The reaction was stirred at RT for 2 h. The reaction was concentrated under reduced pressure and the crude solid obtained was washed with water and 3 mL of THF. The solid was dried under high vacuum to give the title product (0.564 g, 71.4%). m/z 278.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe crude solid obtained
  3. washwas washed with water and 3 mL of THF
  4. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-2a70c79f133849788a881c3d7b482db9
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

Loading…