Water → HCID 68578493, compound

HRID 886952Notes

Reaction equation

HRID 886952 reaction equation
Br[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[F:21][C:22]1([F:27])[CH2:26][CH2:25][NH:24][CH2:23]1.CC(C)([O-])C.[Na+].O>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:21][C:22]1([F:27])[CH2:26][CH2:25][N:24]([C:2]2[C:12]3[O:11][CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:23]1

Participants

7

Reactant 4

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 59403519Tert-butyl 9-bromo-2,3-dihydrobenzo[F][1,4]oxazepine-4(5H)-carboxylate

Product 1

HCID 68578493HCID 68578493, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (328 mg, 1.04 mmol), 3,3-difluoropyrrolidine hydrochloride (150 mg, 1.04 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl(X-phos) m (39.8 mg, 0.0835 mmol), tris(dibenzylideneacetone)dipalladium(0) (19.0 mg, 0.0208 mmol) and sodium tert-butoxide (250 mg, 2.60 mmol) in toluene (10 ml) was stirred under an argon atmosphere at 100° C. for 12 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the desired product (110 mg, 29.8%) as an oil.

Workup

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

Sources & evidence

ORD record
ord-38efd7ddc2174dd1bbe9ada480357c2e
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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