Potassium Carbonate → HCID 19753545, compound

HRID 1588452Notes

Reaction equation

HRID 1588452 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.Br[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[OH-]>CN1CCCC1=O>[CH3:1][N:2]1[CH2:3][CH:4]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=3)[N:10]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:9]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 14923Ammonium HydroxideHCID 113343733-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole

Product 1

HCID 19753545HCID 19753545, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

3-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-5-nitro-1H-indole (4.5 g), 3-bromopyridin (6.0 g), CuBr (4.5 g) and K2CO3 (8.0 g) in N-methyl-2-pyrrolidone (25 ml) were heated under stirring at 160° C. for 2.5 h. After cooling the reaction mixture was poured into diluted NH4OH (500 ml) and extracted with ethyl acetate (3×300 ml). The combined organic phases were dried (MgSO4) and the solvent evaporated. The title compound was obtained by recrystallization from acetone. Yield: 3.4 g (58%). M.p. 175°-177° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with ethyl acetate (3×300 ml)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-f18fc7caea2a4eb783f815049f91306d
Source dataset
uspto-grants-1993_06
Patent number
USRE034299

Reaction notes

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