Tris(1,1-dimethylethyl)phosphine → HCID 66679380, compound

HRID 1964990Notes

Reaction equation

HRID 1964990 reaction equation
Cl[C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[C:12]1B(O)O.[F-].[K+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[O:11]1[C:12]2=[CH:13][CH:14]=[CH:19][C:18]2=[CH:17][CH:16]=[C:15]1[N:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:2]=[C:3]2[CH:4]=[CH:5]1

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 2776266Benzo[b]furan-2-boronic acidHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 66679380HCID 66679380, compound

Reagents, catalysts & solvents 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-7-azaindole (119, 100 mg, 0.66 mmol, prepared as described in Example 70, Scheme 81), 2-Benzofuranboronic acid (212 mg, 1.31 mmol) and Potassium fluoride (127 mg, 2.18 mmol) were stirred in 3 mL of anhydrous dioxane. Tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (10.2 mg, 9.83E-3 mmol) and tri t-butylphosphine (6.6 mg, 0.033 mol) were added and the suspension was stirred at 100° C. for 4 hours in a pressure tube under inert atmosphere. The reaction mixture was cooled to room temperature and was adsorbed onto silica gel and purified by chromatography to provide the compound (120, 56 mg, 36%). MS(ESI) [M+H+]+=235.20.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompurified by chromatography
  3. customto provide the compound (120, 56 mg, 36%)

Sources & evidence

ORD record
ord-cf0057a317194e7c97f8116c5027cb01
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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