Sodium Carbonate → HCID 69056130, compound

HRID 2109515Notes

Reaction equation

HRID 2109515 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:11][N:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14](Cl)[N:13]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:24]B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:11][N:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]([CH3:24])[N:13]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 139377Methylboronic Acid2×HCID 86609495HCID 86609495, compound

Product 1

HCID 69056130HCID 69056130, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of D13 (1.92 g, 5.55 mmol), methylboronic acid, (490 mg, 8.19 mmol) and tetrakis(triphenylphosphine) Pd(0), (315 mg) in dioxan (25 ml) was treated with aqueous sodium carbonate (7 ml). The mixture was heated at reflux for 16 h, allowed to cool, then diluted with water and extracted with DCM (2×50 ml). The organic phase was washed with brine, dried and concentrated to give a solid. T.I.c anlaysis showed that substantial quantities of starting material remained. The crude material was treated again with methylboronic acid, (490 mg, 8.19 mM) and tetrakis(triphenylphosphine) Pd(0), (315 mg) as above. T.I.c. showed complete conversion to the product which was purified by column chromatography to give the title compound as a colourless solid (1.34 g, 74%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperatureto cool
  4. extractionextracted with DCM (2×50 ml)
  5. washThe organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customto give a solid
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cfcc1ba0fb334359ac3a068fcfe9c0de
Source dataset
uspto-grants-2009_04
Patent number
US07514562B2

Reaction notes

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