Cesium carbonate → HCID 86704605, compound

HRID 1508513Notes

Reaction equation

HRID 1508513 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([Cl:13])=[C:11]([CH2:14][O:15][CH3:16])[N:10]=[C:9]([S:17][CH3:18])[N:8]=1)(=O)=O.[CH3:21]B1OB(C)OB(C)O1.C([O-])([O-])=O.[Cs+].[Cs+]>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:13][C:12]1[C:11]([CH2:14][O:15][CH3:16])=[N:10][C:9]([S:17][CH3:18])=[N:8][C:7]=1[CH3:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 574072TrimethylboroxineHCID 86704604HCID 86704604, compound

Product 1

HCID 86704605HCID 86704605, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

A mixture of the title compound from Step B (1.00 g, 2.83 mmol), trimethyl boroxine (1.78 g, 14.18 mmol), Cs2CO3 (0.92 g, 2.83 mmol), and catalytic amount Pd(PPh3)4 was stirred at 140° C. under microwave for 1 h. The solvent was removed. CH2Cl2 and water were added. The organic was extracted with CH2Cl2 (3×10 mL), washed with brine and dried over Na2SO4. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/hexane (1/9) to give as a colorless oil. 1H NMR (CDCl3, 500 MHz) δ 4.61 (s, 2H), 3.55 (s, 3H), 2.60 (s, 3H), 2.58 (s, 3H).

Workup

  1. customThe solvent was removed
  2. additionCH2Cl2 and water were added
  3. extractionThe organic was extracted with CH2Cl2 (3×10 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe residue was purified by column chromatography on silica gel Biotage 40M
  7. washeluting with EtOAc/hexane (1/9)
  8. customto give as a colorless oil

Sources & evidence

ORD record
ord-5320a850265742418768295027d1d05b
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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