Dibenz(b,f)azepine → (Z)-methyl 4-((5H-dibenzo[b,f]azepin-5-yl)methyl)benzoate

HRID 718075

Reaction equation

HRID 718075 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Sn](Cl)(Cl)CCCC)CCC.[CH:27]([C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1)=O.C1([SiH3])C=CC=CC=1>C1COCC1>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:27][C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 9212Dibenz(b,f)azepineHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 59783517(Z)-methyl 4-((5H-dibenzo[b,f]azepin-5-yl)methyl)benzoateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-5H-Dibenzo[b,f]azepine (100 mg, 0.52 mmol), dibutyltin dichloride (54 mg, 0.16 mmol) and methyl 4-formylbenzoate (260 mg, 1.60 mmol) were stirred in THF (2 mL) for 30 minutes. Phenylsilane was added and the reaction mixture was stirred for 3 days. The solvent was evaporated and the residue was purified by flash chromatography (0% to 40% EtOAc in hexanes). The fractions containing some product were washed with Na2S2O4. The layers were split and the organic layer was evaporated to afford title compound 350 (147 mg, 83%) as a yellow solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (0% to 40% EtOAc in hexanes)
  3. additionThe fractions containing some product
  4. washwere washed with Na2S2O4
  5. customThe layers were split
  6. customthe organic layer was evaporated

Sources & evidence

ORD record
ord-7abb1a6f4fef4ff6bddca28cd544f8f0
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Linked notes

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