Water → HCID 19769842, compound

HRID 1590456Notes

Reaction equation

HRID 1590456 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[CH3:5][C:6]1[N:10]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[N:8][C:7]=1[CH2:30][CH:31]1[C:43](=[O:44])[C:42]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[NH:35][C:34]=2[CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:5][C:6]1[N:10]([C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:9]=[N:8][C:7]=1[CH2:30][CH:31]1[C:43](=[O:44])[C:42]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:35]([CH2:3][C:2]#[CH:1])[C:34]=2[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromide2×HCID 11430Potassium CarbonateHCID 19769831HCID 19769831, compound

Product 1

HCID 19769842HCID 19769842, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Propargyl bromide (0.086 ml) was added to a suspension of 1,2,3,9-tetrahydro-3-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl ]-4H-carbazol-4-one (500 mg) and potassium carbonate (265 mg) in acetone (10 ml) and the mixture was stirred under nitrogen for 60 h. More propargyl bromide (0.086 ml) was added and the mixture was stirred at room temperature for 24 h and then at reflux for 6 h. Water (50 ml) was added and the suspension was extracted with dichloromethane (3×25 ml). The combined, dried organic extracts were evaporated to give a gum (650 mg) which was purified by FCC (column made up in ethyl acetate:hexane:triethylamine 80:19:1) eluting with ethyl acetate:hexane (4:1) to give the title compound (95 mg) as a foam, t.l.c. on Et3N impregnated SiO2 (ethyl acetate:hexane 4:1) Rf 0.30.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 h
  2. temperatureat reflux for 6 h
  3. extractionthe suspension was extracted with dichloromethane (3×25 ml)
  4. customdried organic extracts were evaporated

Sources & evidence

ORD record
ord-d11b6ee2976943cfb89f93d5a8e6dff0
Source dataset
uspto-grants-1993_04
Patent number
US05202343

Reaction notes

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