O-Xylene → HCID 66760383, compound

HRID 1850391Notes

Reaction equation

HRID 1850391 reaction equation
C[C:2](C)([O-:4])C.[Na+].C[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1C.[N:15]1([C:22]2[C:23]([CH3:36])=[C:24]([CH3:35])[C:25]3[O:29][C:28]([CH3:31])([CH3:30])[C:27](=[O:32])[C:26]=3[C:33]=2[CH3:34])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:2][O:4][C:13]1[CH:12]=[CH:11][C:10]([N:18]2[CH2:19][CH2:20][CH2:21][N:15]([C:22]3[C:23]([CH3:36])=[C:24]([CH3:35])[C:25]4[O:29][C:28]([CH3:31])([CH3:30])[C:27](=[O:32])[C:26]=4[C:33]=3[CH3:34])[CH2:16][CH2:17]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 23676156Sodium t-butoxideHCID 66760944HCID 66760944, compound

Product 1

HCID 66760383HCID 66760383, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Bis(tri-tert-butylphosphine)palladium (20.0 mg, 0.0387 mmol) and sodium tert-butoxide (500 mg, 5.16 mmol) were added to a solution of o-xylene (20 mL) containing 5-(1,4-diazepan-1-yl)-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one synthesized in Reference Example 63, and the mixture was stirred under argon atmosphere at 120° C. for 12 hours. After cooled to room temperature, the mixture was diluted with water and extracted using ethyl acetate. It was dried using anhydrous magnesium sulfate. After that, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0 to 90:10) to give 240 mg of the title compound (yield: 45%).

Workup

  1. customsynthesized in Reference Example 63
  2. temperatureAfter cooled to room temperature
  3. extractionextracted
  4. customIt was dried
  5. customAfter that, the solvent was removed under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0 to 90:10)

Sources & evidence

ORD record
ord-43f1623798e04e79b2269affdcf66c60
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

Loading…