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Tris(1,1-dimethylethyl)phosphine → HCID 57703182, compound

HRID 1514013
Notes
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Reaction equation

HRID 1514013 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[O:14][C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]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:9]5=[N:10][CH:11]=[CH:12][CH:13]=[C:8]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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 5462222PotassiumHCID 123753316-Chlorobenzofuro[2,3-b]pyridineHCID 132360223,9'-Bicarbazole

Product 1

HCID 57703182HCID 57703182, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 7237O-XyleneSolvent

Procedure

The 300 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 6-chlorobenzofuro[2,3-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, 20 mmol) 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 36 hours. Then the reaction was cooled down to room temperature, washed with water, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 4:1, providing 3.01 g of 6-(9H-3,9′-bicarbazol-9-yl)benzofuro[2,3-b]pyridine as white solid, structure was confirmed by NMR and MS spectroscopy.

Workup

  1. customThe 300 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. washwashed with water
  7. filtrationfiltered through silica plug
  8. customevaporated

Sources & evidence

ORD record
ord-42f8c6c422dc43fd936d5e4280b0c5b1
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08221905B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes