Potassium Carbonate → HCID 86609098, compound

HRID 902293Notes

Reaction equation

HRID 902293 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16](OS(C(F)(F)F)(=O)=O)[CH:17]=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>O1CCOCC1.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>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:33]4[CH:34]=[C:35]([Cl:38])[CH:36]=[CH:37][C:32]=4[Cl:31])[CH:17]=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 27733712,5-Dichlorobenzeneboronic acidHCID 86609099HCID 86609099, compound

Product 1

HCID 86609098HCID 86609098, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ((2R)-8-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate (0.50 g, 1.1 mmol), 2,5-dichlorophenylboronic acid (0.42 g, 2.2 mmol), potassium carbonate (0.46 g, 3.3 mmol) and lithium chloride (0.14 g, 3.3 mmol) in dioxane (3.75 ml) and water (1.25 mL) was purged with nitrogen for 30 minutes. Tetrakis(triphenylphosphine)palladium (0) (60 mg, 0.052 mmol) was added and the reaction mixture heated at 100° C. for 4 hours. The cooled reaction mixture was then partitioned between ethyl acetate (15 mL) and 1 M aqueous sodium hydroxide (15 mL). The organic layer was separated, washed with saturated brine (15 mL) dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford an orange oil. Purification by flash chromatography using a solvent gradient of 5 to 20% ethyl acetate in hexane gave 0.46 g (90%) of [(2R)-8-(2,5-dichlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as an off-white solid. HRMS: calcd for C23H20Cl2O4S+H+, 463.05321. found (ESI, [M+H]+), 463.0553.

Workup

  1. customwas purged with nitrogen for 30 minutes
  2. customThe cooled reaction mixture
  3. customwas then partitioned between ethyl acetate (15 mL) and 1 M aqueous sodium hydroxide (15 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated brine (15 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford an orange oil
  10. customPurification by flash chromatography

Sources & evidence

ORD record
ord-8d0911aaee724ec7ae336bb635926ec7
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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