Potassium Carbonate → HCID 86698765, compound

HRID 338433Notes

Reaction equation

HRID 338433 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.[C:19](=O)([O-])[O-:20].[K+].[K+].Br[C:26]1[CH:35]=[CH:34][C:29]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][C:27]=1[F:36]>CN(C=O)C.O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:19]=[O:20])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:26]1[CH:35]=[CH:34][C:29]([O:30][CH2:31][CH2:32][OH:33])=[CH:28][C:27]=1[F:36]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 652040252-(4-Bromo-3-fluorophenoxy)ethanolHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Product 1

HCID 86698765HCID 86698765, compoundYield 31.5%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (100 mg, 0.38 mmol) and N,N-dimethylformiminium chloride (97 mg, 0.76 mmol) in DMF (3 mL) and dioxane (0.6 mL) was stirred at room temperature for 30 min. Potassium carbonate (2 mL, 4 mmol, 2 N) was added to the mixture. Then 2-(4-bromo-3-fluorophenoxy)ethanol (96 mg, 0.38 mmol) and Pd(dppf)Cl2 (20 mg, 0.03 mmol) was added to the reaction. The mixture was degassed by passing nitrogen through the solution for 5 min. and stirred at 80° C. for 2 hrs. The reaction was cooled and concentrated. The residue was dissolved by EtOAc (100 mL), washed with water (30 mL), saturated NH4Cl (30 mL), brine (30 mL), dried over sodium sulfate and concentrated to afford a crude product. The crude was further purified by silica gel chromatography (PE/EtOAc=20% to 50%) to give the title compound (40 mg, 31% yield) as a light yellow oil.

Workup

  1. customThe mixture was degassed
  2. customfor 5 min.
  3. stirringstirred at 80° C. for 2 hrs
  4. temperatureThe reaction was cooled
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved by EtOAc (100 mL)
  7. washwashed with water (30 mL), saturated NH4Cl (30 mL), brine (30 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto afford a crude product
  11. customThe crude was further purified by silica gel chromatography (PE/EtOAc=20% to 50%)

Sources & evidence

ORD record
ord-f330328503bf4be2a1492dc32c19bd10
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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