4-Fluorobenzoyl chloride → 6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-2-[(E)-2-phenylethenyl]-4H-oxazolo[4,5-d]azepine

HRID 1529578Notes

Reaction equation

HRID 1529578 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]1(/[CH:17]=[CH:18]/[C:19]2[O:20][C:21]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23][C:22]=3[N:28]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:25]2[CH2:26][CH2:27][C:21]3[O:20][C:19](/[CH:18]=[CH:17]/[C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:28][C:22]=3[CH2:23][CH2:24]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 666089425,6,7,8-tetrahydro-2-[(E)-2-phenylethenyl]-4H-oxazolo[4,5-d]azepine

Product 1

HCID 666092096-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-2-[(E)-2-phenylethenyl]-4H-oxazolo[4,5-d]azepineYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

4-Fluorobenzoyl chloride (0.016 mL, 0.14 mmol) was added dropwise to a stirred solution of 5,6,7,8-tetrahydro-2-[(E)-2-phenylethenyl]-4H-oxazolo[4,5-d]azepine (95 mg, 0.13 mmol) and TEA (0.026 mL, 0.19 mmol) in DCM (1 mL) at 0° C. The reaction mixture was stirred at room temperature for 15 minutes and then diluted with a saturated solution of NaHCO3. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo. The crude product was triturated with DIPE to yield 6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-2-[(E)-2-phenylethenyl]-4H-oxazolo[4,5-d]azepine (37 mg, 80% yield) as a white solid. C22H19FN2O2.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvents evaporated in vacuo
  5. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50)
  6. customThe desired fractions were collected
  7. customthe solvents evaporated in vacuo
  8. customThe crude product was triturated with DIPE

Sources & evidence

ORD record
ord-9c2e45bd5968493281e8312a0e969174
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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