Potassium Carbonate → HCID 68580484, compound

HRID 886978Notes

Reaction equation

HRID 886978 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:20])=[C:18](Br)[C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]1(B(O)O)[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[CH2:1]([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][C:17]([F:20])=[C:18]([CH:21]3[CH2:23][CH2:22]3)[C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2760897Cyclopropylboronic acidHCID 68577855HCID 68577855, compound

Product 1

HCID 68580484HCID 68580484, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 4-benzyl-9-bromo-8-fluoro-2,3,4,5-tetrahydro-1,4-benzoxazepine (500 mg, 1.49 mmol), cyclopropylboronic acid (153 mg, 1.78 mmol), potassium carbonate (617 mg, 4.46 mmol), dioxane (3 ml) and water (3 ml) was deaerated with argon gas, and bis(triphenylphosphine)palladium(2) dichloride (52.2 mg, 0.0744 mmol) was added. The mixture was stirred under an argon atmosphere for 3 hr at 100° C. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product (408 mg, 92.1%) as an oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2894603eaab34ae5a7e72fea390e6f04
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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