Tris(1,1-dimethylethyl)phosphine → HCID 57703127, compound

HRID 1514016Notes

Reaction equation

HRID 1514016 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:13]3[C:8](=[N:9][CH:10]=[CH:11][CH:12]=3)[C:6]=2[CH:7]=1.[CH:15]1[C:27]2[N:26]([C:28]3[CH:29]=[CH:30][C:31]4[NH:32][C:33]5[C:38]([C:39]=4[CH:40]=3)=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[K]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C(C)=CC=CC=1>[CH:30]1[C:31]2[N:32]([C:2]3[CH:3]=[CH:4][C:5]4[O:14][C:13]5[C:8](=[N:9][CH:10]=[CH:11][CH:12]=5)[C:6]=4[CH:7]=3)[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:39]=2[CH:40]=[C:28]([N:26]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:19]3[C:27]2=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:29]=1

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 5462222PotassiumHCID 132360229H-3,9'-BicarbazoleHCID 687342158-Chlorobenzofuro[3,2-b]pyridine

Product 1

HCID 57703127HCID 57703127, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolvent

Procedure

The 100 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 8-chlorobenzofuro[3,2-b]pyridine (2.04 g, 10 mmol), 3-(9-carbazolyl)carbazole (3.32 g, 10 mmol), Pd(OAc)2 (450 mg, 20 mol %), P(t-Bu)3 (10 mL of 1M solution in toluene, 10 mmol), potassium tert-buthoxide (1.92 g, 1.5 eq) and 150 ml of xylene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 24 hours. Then reaction was cooled down to room temperature, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 9:1, providing 2.5 g of 8-(9H-3,9′-bicarbazol-9-yl)benzofuro[3,2-b]pyridine as white solid. The structure was confirmed by NMR and MS spectroscopy.

Workup

  1. customThe 100 mL round bottom flask, equipped with magnetic stirrer
  2. temperaturerefluxed condenser
  3. additionThe flask was filled with nitrogen
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux
  6. customThen reaction
  7. filtrationfiltered through silica plug
  8. customevaporated

Sources & evidence

ORD record
ord-c21a053752d64d07aa619c4f9a9f9fb5
Source dataset
uspto-grants-2012_07
Patent number
US08221905B2

Reaction notes

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