Isopentyltriphenylphosphonium bromide → 2-(3,4-Difluorophenyl)-4-(6-methyl-3-heptenyl)-5-[4-(methylsulfonyl)phenyl]-3(2h)-pyridazinone

HRID 891313노트

반응식

HRID 891313 반응식
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH:4]([CH3:6])[CH3:5].CC(C)([O-])C.[K+].[F:32][C:33]1[CH:34]=[C:35]([N:40]2[C:45](=[O:46])[C:44]([CH2:47][CH2:48][CH:49]=O)=[C:43]([C:51]3[CH:56]=[CH:55][C:54]([S:57]([CH3:60])(=[O:59])=[O:58])=[CH:53][CH:52]=3)[CH:42]=[N:41]2)[CH:36]=[CH:37][C:38]=1[F:39]>C1(C)C=CC=CC=1>[F:32][C:33]1[CH:34]=[C:35]([N:40]2[C:45](=[O:46])[C:44]([CH2:47][CH2:48][CH:49]=[CH:2][CH2:3][CH:4]([CH3:6])[CH3:5])=[C:43]([C:51]3[CH:56]=[CH:55][C:54]([S:57]([CH3:60])(=[O:58])=[O:59])=[CH:53][CH:52]=3)[CH:42]=[N:41]2)[CH:36]=[CH:37][C:38]=1[F:39]

참가 물질

5

반응물 3

HCID 2759379Isopentyltriphenylphosphonium bromideHCID 219341612-(3,4-Difluorophenyl)-4-(2-formylethyl)-5-[4-(methylsulfonyl)phenyl]-3(2h)-pyridazinoneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 537185062-(3,4-Difluorophenyl)-4-(6-methyl-3-heptenyl)-5-[4-(methylsulfonyl)phenyl]-3(2h)-pyridazinone수율 13%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of isoamyltriphenylphosphonium bromide (414 mg, 1 mmol) and potassium t-butoxide (112 mg, 1 mmol) in toluene (25 mL) was refluxed for 30 minutes and then cooled to room temperature. The crude aldehyde was added and the mixture was refluxed for 14 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate and was washed with water, 10% citric acid, brine, dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (silica gel, 1:1 hexanes-ethyl acetate) provided the title compound as an oil (yield: 120 mg, 13%). 1H NMR (300 MHz, DMSO-d6) δ 0.74 (d, J=7 Hz, 6H), 1.44 (m, 1H), 1.70 (t, J=7 Hz, 2H), 2.22 (m, 2H), 2.54 (m, 2H); 3.30 (s, 3H), 5.29 (m, 2H), 7.51 (m, 1H), 7.63 (m, 1H), 7.74 (d, J=9 Hz, 2H), 7.82 (m, 1H), 8.02 (s, 1H), 8.10 (d, J=9 Hz, 2H). MS (APCI+) m/z 473 (M+H)+ and (APCI−) m/z 471 (M−H)−, m/z 507 (M+Cl)−. Anal. calc. for C25H26F2N2O3S: C, 63.54; H, 5.54; N, 5.92. Found: C, 63.74; H, 5.67; N, 5.58.

후처리

  1. temperaturewas refluxed for 30 minutes
  2. temperaturethe mixture was refluxed for 14 hours
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwas washed with water, 10% citric acid, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customPurification by column chromatography (silica gel, 1:1 hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-e43a30cb5ffb4d7188d5b920591c6844
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001895B2

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