Potassium Carbonate → HCID 86698769, compound

HRID 1054779Notes

Reaction equation

HRID 1054779 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:31]=[CH:30][C:29]([C:32]2([C:35]([OH:37])=[O:36])[CH2:34][CH2:33]2)=[CH:28][CH:27]=1>O1CCOCC1.CN(C=O)C.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:31]=[CH:30][C:29]([C:32]2([C:35]([OH:37])=[O:36])[CH2:34][CH2:33]2)=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acidHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Product 1

HCID 86698769HCID 86698769, compoundYield 131.1%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (152 mg, 0.577 mmol) in anhydrous dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (170 mg, 1.33 mmol). The reaction mixture was stirred at room temperature for 20 mins. A thick solution was observed after 20 mins. 2 N potassium carbonate (400 mg, 2.90 mmol), 1-(4-bromophenyl)cyclopropanecarboxylic acid (137 mg, 0.568 mmol) and Pd(dppf)Cl2 (50 mg, 0.068 mmol) were then added. The reaction was degassed with N2 for 2 minutes. The reaction was then heated to 90° C. for 30 minutes. The mixture was poured into water (60 mL) and the layers separated. The aqueous layer was extracted with ethyl acetate (50 mL×2). The aqueous phase was acidified to pH=5 with 1 N HCl and then extracted with ethyl acetate (50 mL×3). The combined organic phases were washed with brine (50 mL), dried and concentrated to give the title compound (253 mg, quantitative yield) as a brown oil, which was used in the next step without further purification.

Workup

  1. waitA thick solution was observed after 20 mins
  2. customThe reaction was degassed with N2 for 2 minutes
  3. temperatureThe reaction was then heated to 90° C. for 30 minutes
  4. additionThe mixture was poured into water (60 mL)
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (50 mL×2)
  7. extractionextracted with ethyl acetate (50 mL×3)
  8. washThe combined organic phases were washed with brine (50 mL)
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1c94c8b2ed8546028841b1874e44d237
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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