Potassium Phosphate, Tribasic → HCID 86684645, compound

HRID 717996Notes

Reaction equation

HRID 717996 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[C:13]3[O:14][C:15]4[C:20]([CH:21]([CH3:23])[CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=4[C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:32][C:33]1(C)[C:37](C)(C)OB(C(C)=C)O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.O.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.[Pd].[Pd]>[CH:21]([C:20]1[C:15]2[O:14][C:13]3[C:8]([C:4]4[CH:3]=[C:2]([C:33]([CH3:37])=[CH2:32])[CH:7]=[CH:6][N:5]=4)=[CH:9][CH:10]=[CH:11][C:12]=3[C:16]=2[CH:17]=[CH:18][CH:19]=1)([CH3:23])[CH3:22]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86684646HCID 86684646, compound

Product 1

HCID 86684645HCID 86684645, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

4-chloro-2-(6-isopropyldibenzo[b,d]furan-4-yl)pyridine (10.5 g, 32.6 mmol) and potassium phosphate (22.54 g, 98 mmol) were dissolved in 500 mL of toluene and 50 mL of water. The reaction was purged with nitrogen for 20 minutes and then 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (6.13 mL, 32.6 mmol), Pd2(dba)3 (0.598 g, 0.653 mmol) and dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.072 g, 2.61 mmol) were added. The reaction was refluxed for 18 hours. After cooling the reaction to room temperature, 100 mL of water was added to the reaction mixture. The aqueous layer was extracted twice with 100 mL of ethyl acetate. The organic layer was passed through a plug of silica gel, eluting with DCM. After evaporation of the solvent, the crude product was subjected to column chromatography (SiO2, 3% ethyl acetate in hexane to 5% ethyl acetate in hexane, v/v) to yield 6.3 g (60.1%) of pure product.

Workup

  1. customThe reaction was purged with nitrogen for 20 minutes
  2. temperatureThe reaction was refluxed for 18 hours
  3. temperatureAfter cooling
  4. customthe reaction to room temperature
  5. extractionThe aqueous layer was extracted twice with 100 mL of ethyl acetate
  6. washeluting with DCM
  7. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-dae90798834643da8e33b67b7ebe1209
Source dataset
uspto-grants-2015_11
Patent number
US09193745B2

Reaction notes

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