Potassium Iodide → 3-Cyclobutyl-7-(2,4-difluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 645816노트

반응식

HRID 645816 반응식
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([N:11]2[CH2:17][CH2:16][C:15]3[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:14]=3[CH2:13][CH2:12]2)[CH2:10][CH2:9][CH2:8]1.[F:23][C:24]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:25]=1[CH2:26]Br.[I-].[K+]>CC(=O)CC>[CH:7]1([N:11]2[CH2:17][CH2:16][C:15]3[CH:18]=[C:19]([O:22][CH2:26][C:25]4[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:24]=4[F:23])[CH:20]=[CH:21][C:14]=3[CH2:13][CH2:12]2)[CH2:10][CH2:9][CH2:8]1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

생성물 1

HCID 104051733-Cyclobutyl-7-(2,4-difluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

Potassium carbonate (778 mg, 5.6 mmol) was added to a stirred solution of 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol (E3) (868 mg, 4.0 mmol), 2,4-difluorobenzyl bromide (0.25 ml, 2.1 mmol) and potassium iodide (25 mg) in butanone (9 ml). The reaction mixture was stirred at reflux for 18 hours, cooled, filtered and concentrated in vacuo. The crude residue was dissolved with ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification of the resulting residue by column chromatography eluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5 then 1:9:10) afforded the title compound (E79); MS (ES+) m/e 344 [M+H]+.

후처리

  1. temperatureat reflux for 18 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude residue was dissolved with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification of the resulting residue by column chromatography
  11. washeluting with a mixture of 0.880 ammonia:ethanol:dichloromethane (0.25:2.25:97.5

출처 및 근거

ORD 기록
ord-fcd65ff85acc465da9b98c4e77053948
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704994B2

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