Toluene → HCID 68579342, compound

HRID 886966Notes

Reaction equation

HRID 886966 reaction equation
Br[C:2]1[C:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:31][C@H:32]1[CH2:37][O:36][CH2:35][CH2:34][NH:33]1.CC(C)([O-])C.[Na+].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].O>[CH3:31][C@H:32]1[CH2:37][O:36][CH2:35][CH2:34][N:33]1[C:4]1[CH:3]=[CH:2][C:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 23676156Sodium t-butoxideHCID 68578195HCID 68578195, compoundHCID 86640608HCID 86640608, compound

Product 1

HCID 68579342HCID 68579342, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

A solution of tert-butyl 6-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (500 mg, 1.52 mmol), (3S)-3-methylmorpholine p-toluenesulfonate (416 mg, 1.52 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl(X-phos) (58.0 mg, 0.122 mmol), tris(dibenzylideneacetone)dipalladium(0) (27.8 mg, 0.0304 mmol), sodium tert-butoxide (365 mg, 3.80 mmol) and toluene (6 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 (420 mg, 79.2%) 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-d45482825a3040898ec2cb183c3cd470
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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