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

HRID 1647812Notes

Reaction equation

HRID 1647812 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 6 h. 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 6 h
  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-1b6cf89034034fbaa6b800996a956c52
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

Loading…