Indole → 3-(2-Chloro-5-methylpyrimidin-4-yl)-1H-indole

HRID 1255986Notes

Reaction equation

HRID 1255986 reaction equation
C[Mg]I.[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([CH3:21])=[CH:16][N:15]=1.O>ClCCCl>[Cl:13][C:14]1[N:19]=[C:18]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4][CH:5]=2)[C:17]([CH3:21])=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 178418373HCID 178418373, compound

Product 1

HCID 580714243-(2-Chloro-5-methylpyrimidin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methylmagnesium iodide (3 M in diethyl ether, 30.7 mL, 92.02 mmol) was added over 20 min to a solution of 1H-indole (7.19 g, 61.35 mmol) in DCE (25 mL) under nitrogen at 0° C. 2,4-Dichloro-5-methylpyrimidine (10 g, 61.35 mmol) in DCE (20 mL) was then added slowly to the reaction mixture over 20 min at 0° C. and the reaction mixture was stirred for an additional 30 min at 0° C. The reaction mixture was then allowed to warm up to RT and stirred at 30 min. The reaction mixture was then cooled to 0° C. and water (50 mL) was slowly added. The resultant yellow solids were collected by vacuum filtration. The solids were then suspended in 10% aqueous citric acid solution (150 mL) and stirred for 10 min, filtered, then washed with water and diethyl ether to give the title product. (8.10 g, 54.2%) as a yellow solid.

Workup

  1. temperatureto warm up to RT
  2. stirringstirred at 30 min
  3. temperatureThe reaction mixture was then cooled to 0° C.
  4. filtrationThe resultant yellow solids were collected by vacuum filtration
  5. stirringstirred for 10 min
  6. filtrationfiltered
  7. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-cad46745ab8e4405bef9c5531d5c3d54
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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