Diisopropylethylamine → 3-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-nitro-1H-indole

HRID 1463356Notes

Reaction equation

HRID 1463356 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15]Br)([O-:3])=[O:2].[CH3:17][O:18][C:19]1[C:20]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:21][CH:22]=[N:23][CH:24]=1.C(N(C(C)C)CC)(C)C>C(#N)C.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[C:20]([N:25]2[CH2:30][CH2:29][N:28]([CH2:15][CH2:14][CH2:13][C:7]3[C:6]4[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[NH:9][CH:8]=3)[CH2:27][CH2:26]2)=[N:21][CH:22]=[N:23][CH:24]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 104201525-Methoxy-4-(piperazin-1-yl)pyrimidineHCID 199620433-(3-Bromopropyl)-5-nitro-1H-indole

Product 1

HCID 199620393-[3-[4-(5-Methoxy-4-pyrimidyl)-1-piperazinyl]propyl]-5-nitro-1H-indoleYield 70%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-nitro-3-(3-bromopropyl)indole (0.57 g, 2.0 mmol), 1-(5-methoxy-4-pyrimidyl) piperazine (0.47 g, 2.4 mmol), KI (0.40 g, 2.4 mmol) and diisopropylethylamine (1.75 mL, 10.0 mmol) in 20 mL of acetonitrile was refluxed under Ar for 6h. The cooled reaction mixture was diluted with ethyl acetate and washed (H2O, brine). The aqueous wash was back-extracted with CH2Cl2 and the organic phase was washed (H2O, brine). The combined organic phases were dried (Na2SO4) and evaporated, and the residue was chromatographed (SiO2 /CH2Cl2 -MeOH, 95:5) to give a solid. This material was triturated with CH2Cl2 -hexane to give the title compound (0.55 g, 70%) as a yellow solid, m.p. 163°-166° C.

Workup

  1. temperaturewas refluxed under Ar for 6h
  2. customThe cooled reaction mixture
  3. washwashed (H2O, brine)
  4. washThe aqueous wash
  5. extractionwas back-extracted with CH2Cl2
  6. washthe organic phase was washed (H2O, brine)
  7. dry with materialThe combined organic phases were dried (Na2SO4)
  8. customevaporated
  9. customthe residue was chromatographed (SiO2 /CH2Cl2 -MeOH, 95:5)
  10. customto give a solid
  11. customThis material was triturated with CH2Cl2 -hexane

Sources & evidence

ORD record
ord-a3e13b58cd5949bfaa98a235b7186e53
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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