Potassium Carbonate → HCID 25263858, compound

HRID 563120Notes

Reaction equation

HRID 563120 reaction equation
Br[C:2]1[CH:16]=[C:15]2[C:5]([C:6](=[O:18])[C:7](=[O:17])[C:8]3[S:13][CH2:12][CH:11]([CH3:14])[O:10][C:9]=32)=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:14][CH:11]1[O:10][C:9]2[C:15]3[C:5]([C:6](=[O:18])[C:7](=[O:17])[C:8]=2[S:13][CH2:12]1)=[CH:4][CH:3]=[C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:16]=3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 57775486HCID 57775486, compound

Product 1

HCID 25263858HCID 25263858, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 9-bromo-2-methyl-2,3-dihydronaphtho[1,2-b][1,4]oxathiine-5,6-dione (0.1 g, 0.31 mmol) in 1,4-dioxane (1.0 mL) was added phenylboronic acid (0.056 g, 0.459 mmol), potassium carbonate (0.118 g, 0.857 mmol) and 1,1′-bis[di(t-butylphosphine)ferrocene]PdCl (0.02 g, 0.031 mmol). The reaction mixture was heated at 90° C. for 6 hours. The resulting mixture was filtered and solvent removed under reduced pressure. The crude mixture was purified by flash column chromatography (SiO2, 16% EtOAc in hexanes) to give the product as a purple solid (0.024 g, 20%). M.p.=190-192° C.; 400 MHz 1H NMR (CDCl3) δ: 8.11 (d, J=7.6, 1H), 7.93 (d, J=1.6, 1H), 7.66 (m, 3H), 7.45 (m, 3H), 4.70 (m, 1H), 3.11 (d, J=13.2, 1H), 2.94 (m, 1H), 1.65 (m, 3H); LCMS: 323 [M+H].

Workup

  1. filtrationThe resulting mixture was filtered
  2. customsolvent removed under reduced pressure
  3. customThe crude mixture was purified by flash column chromatography (SiO2, 16% EtOAc in hexanes)

Sources & evidence

ORD record
ord-20eac2ee104449b58a87ddedf229eda5
Source dataset
uspto-grants-2011_11
Patent number
US08067459B2

Reaction notes

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