Cesium carbonate → HCID 57419565, compound

HRID 2353252Notes

Reaction equation

HRID 2353252 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 696764-IodoanisoleHCID 8690650HCID 8690650, compound

Product 1

HCID 57419565HCID 57419565, compoundYield 11.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the compound from step 1 (0.59 g, 2 mmol) and 1-iodo-4-methoxy-benzene (0.47 g, 2 mmol) in anhydrous dioxane (8 mL) were added cesium carbonate (1.26 g, 4 mmol), N,N-dimethylglycine. HCl (0.036 g, 0.25 mmol), and copper (I) iodide (0.015 g, 0.078 mmol) and the reaction mixture was stirred at 90° C. for 24 h under nitrogen. The mixture was filtered and partitioned between ethyl acetate (153 mL) and water (100 mL). The organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated to give a off-white oil, which was purified by silica gel flash chromatography to afford the title product (85 mg, 11.4%) as a light yellow solid: MS (ESI) m/z 359 (M+H). 1H NMR (400 MHz, CDCl3) δ 2.62 (t, J=4.8 Hz, 4H), 3.14 (t, J=4.8 Hz, 4H), 3.57 (s, 2H), 3.78 (s, 3H), 6.83-6.93 (m, 8H), 7.30-7.34 (m, 5H).

Workup

  1. filtrationThe mixture was filtered
  2. custompartitioned between ethyl acetate (153 mL) and water (100 mL)
  3. washThe organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give a off-white oil, which
  7. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-9fd9dd758a2a46b383c4ed8d8ca70d5f
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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