Cesium carbonate → HCID 23634440, compound

HRID 1023204Notes

Reaction equation

HRID 1023204 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:16][CH2:17][O:18][CH3:19])[C:6]1[C:7]([C:14]#[N:15])=[N:8][C:9]([Cl:13])=[C:10](Br)[N:11]=1.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>CCOC(C)=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].C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:16][CH2:17][O:18][CH3:19])[C:6]1[C:7]([C:14]#[N:15])=[N:8][C:9]([Cl:13])=[C:10]([C:21]2[O:20][CH:24]=[CH:23][CH:22]=2)[N:11]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 2734357Furan-2-boronic acidHCID 24852692HCID 24852692, compound

Product 1

HCID 23634440HCID 23634440, compoundYield 78.3%

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 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of the product from step 4 (1.0 g, 2.87 mmol), 2-furanboronic acid (643 mg, 5.75 mmol), Cs2CO3 (3.31 g, 10.2 mmol), TFP (35 mol %, 236 mg, 1.02 mmol), and Pd2 dba3-CHCl3 (5 mol %, 10 mol % Pd, 150 mg) was subjected to 3 vacuum/Argon cycles and placed under a positive pressure of Argon. Anhydrous dioxane (50 mL) was added and the reaction mixture was heated to 75° C. for 16 h thereafter. The reaction mixture was cooled to room temperature, diluted with EtOAc (100 mL) and filtered through a medium frit. Concentration and purification of the residue by flash chromatography (SiO2, 50/1 CHCl3-MeOH) afforded the 757 mg of the furan adduct (78% yield) as a tan powder: LCMS (5-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time=6.41 min on 250 mm column, (M+H)+=337.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a medium frit
  3. concentrationConcentration and purification of the residue by flash chromatography (SiO2, 50/1 CHCl3-MeOH)

Sources & evidence

ORD record
ord-3b6527c5603c4edd95a956e2fd411337
Source dataset
uspto-grants-2014_05
Patent number
US08722685B2

Reaction notes

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