Carbon Dioxide → HCID 18965678, compound

HRID 1656276Notes

Reaction equation

HRID 1656276 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)[CH:2]=[CH2:3].[C:14]([Li])([CH3:17])([CH3:16])[CH3:15].[Bi](Cl)(Cl)Cl.C(=O)=O.[BiH3:26]>C(OCC)C.C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Bi:26]([C:9]3[CH:8]=[C:7]4[C:12](=[CH:11][CH:10]=3)[N:4]([CH2:1][CH:2]=[CH2:3])[CH:5]=[CH:6]4)[C:6]3[CH:15]=[C:14]4[C:17](=[CH:8][CH:7]=3)[N:4]([CH2:1][CH:2]=[CH2:3])[CH:5]=[CH:16]4)=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)[CH:2]=[CH2:3]

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 9242BismuthineHCID 24591Bismuth trichlorideHCID 189656835-Bromo-1-(prop-2-en-1-yl)-1H-indoleHCID 178418306HCID 178418306, compound

Product 1

HCID 18965678HCID 18965678, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 1-allyl-5-bromoindole (730 mg., 3.09 mmol., 1 eq.) in diethyl ether (15 mL) at -78° C. under N2 was added t-butyllithium (1.8 mL., 3.09 mmol., 1 eq., 1.7M solution in pentane). The mixture was stirred at -78° C. under N2 for 1 h. To this mixture was added a solution of bismuth trichloride (292 mg., 0.93 mmol., 0.3 eq.) in dry THF (3 mL.) dropwise via syringe. The ice bath was packed with dry ice and the flask covered. The mixture was allowed to warm slowly to room temperature overnight. The reaction mixture was then diluted with toluene and washed with brine. The layers were separated and the aqueous layer extracted 3× with toluene. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in ether and filtered through a 0.4 micron pTFE membrane. The product started to crystallize. Cooled solution in freezer. Collected crystals giving 200 mg. of tris-1-allylindol-5-yl)bismuthine.

Workup

  1. temperatureto warm slowly to room temperature overnight
  2. washwashed with brine
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted 3× with toluene
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in ether
  9. filtrationfiltered through a 0.4 micron pTFE membrane
  10. customto crystallize
  11. customCollected crystals
  12. customgiving 200 mg

Sources & evidence

ORD record
ord-8aa5c4f2db744114b7280a95d7354f46
Source dataset
uspto-grants-1993_10
Patent number
US05252732

Reaction notes

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