Sodium Carbonate → HCID 24987023, compound

HRID 2251660Notes

Reaction equation

HRID 2251660 reaction equation
[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:9]=2)[C:4](=[O:19])[CH2:3]1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:4](=[O:19])[CH2:3][C:2]3([CH3:20])[CH3:1])=[CH:24][CH:23]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 57618520Trifluoromethanesulfonic acid 3,3-dimethyl-1-oxo-indan-5-yl ester

Product 1

HCID 24987023HCID 24987023, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred solution of trifluoro-methanesulfonic acid 3,3-dimethyl-1-oxo-indan-5-yl ester (0.25 g, 0.81 mmol) in glyme (7 mL) was added 4-chlorophenyl boronic acid (0.19 g, 1.22 mmol), a solution of sodium carbonate (0.26 g, 2.43 mmol) in water (1.5 mL), and tetrakis(triphenylphosphine)palladium (0) (0.05 g, 0.04 mmol). The resulting solution was heated to reflux for 2 hours. The mixture was cooled to room temperature, concentrated, taken up in ethyl acetate and filtered through a pad of the Celite® reagent. The filtrate was concentrated and the residue was purified by Gilson high performance liquid chromatography (HPLC—10 to 100 acetonitrile in water) to afford 5-(4-chlorophenyl)-3,3-dimethylindan-1-one as a white solid. (0.11 g, 50%). MS (ES) m/z 271.0; HRMS: calcd for C17H15ClO+H+, 271.0884; found (ESI, [M+H]+), 271.0877.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated
  4. filtrationfiltered through a pad of the Celite® reagent
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by Gilson high performance liquid chromatography (HPLC—10 to 100 acetonitrile in water)

Sources & evidence

ORD record
ord-21d802e978514e47ba0f86a5e0c09d2b
Source dataset
uspto-grants-2008_01
Patent number
US07319152B2

Reaction notes

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