Sodium Carbonate → HCID 58498974, compound

HRID 1471179Notes

Reaction equation

HRID 1471179 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18](=[O:20])[CH3:19].[C:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])[CH3:22]>O.C1(C)C=CC=CC=1.C(O)C.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>[C:18]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[CH:15]=[CH:16][CH:17]=[C:8]2[C:27]1[CH:28]=[CH:29][C:24]([C:21](=[O:23])[CH3:22])=[CH:25][CH:26]=1)(=[O:20])[CH3:19]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 57455306HCID 57455306, compound

Product 1

HCID 58498974HCID 58498974, compoundYield 94.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of sodium carbonate (2.55 g, 24.09 mmol) in water (20 mL) was added to a solution of 1-(5-bromonaphthalen-1-yl)ethanone (1.2 g, 4.8 mmol) and 4-acetylphenylboronic acid (1.03 g, 6.26 mmol) in toluene (20 mL) and ethanol (20 mL) and then heterogeneous solution was vigorously stirred with bubbling nitrogen for 15 min. Then Pd(PPh3)4 (0.111 g, 0.096 mmol) was added and the reaction vessel was sealed and heated at reflux for 6 h. The reaction was cooled and concentrated to dryness. The crude residue was taken into EtOAc (˜150 mL) and water (˜100 mL). The layers were separated and the organic layer was washed with brine, dried (MgSO4), filtered and concentrated to an orange solid. The orange solid was purified on a BIOTAGE® Horizon (40 g SiO2, DCM) to yield 1-(4-(5-acetylnaphthalen-1-yl)phenyl)ethanone (1.31 g) as an off-white solid. LC-MS retention time 3.736 min; m/z 289.19 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 3u C18 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where Solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and Solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a MICROMASS® Platform for LC in electrospray mode. 1H NMR (400 MHz, chloroform-d) δ ppm 8.75 (d, J=8.8 Hz, 1 H), 8.11 (d, J=8.5 Hz, 2 H), 7.99 (d, J=8.5 Hz, 1 H), 7.94 (dd, J=7.2, 1.1 Hz, 1 H), 7.67 (dd, J=8.5, 7.0 Hz, 1 H), 7.58 (d, J=8.3 Hz, 2 H), 7.45-7.51 (m, 2 H), 2.79 (s, 3 H), 2.70 (s, 3 H).

Workup

  1. customthe reaction vessel was sealed
  2. temperatureheated
  3. temperatureat reflux for 6 h
  4. temperatureThe reaction was cooled
  5. concentrationconcentrated to dryness
  6. customThe layers were separated
  7. washthe organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated to an orange solid
  11. customThe orange solid was purified on a BIOTAGE® Horizon (40 g SiO2, DCM)

Sources & evidence

ORD record
ord-18876802ebba4784bff7585ae3619c7e
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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