4-Fluorobenzylamine → 5,6-bis(Benzyloxy)-N-[(4-fluorophenyl)methyl]pyridazin-3-amine

HRID 927096

반응식

HRID 927096 반응식
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Cl-].[Cl-].[Fe+2].[Pd+2].O1CCOCC1>[CH2:16]([O:15][C:14]1[CH:13]=[C:12]([NH:36][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([F:30])=[CH:32][CH:33]=2)[N:11]=[N:10][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 673264-FluorobenzylamineHCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2회HCID 23676156Sodium t-butoxide

생성물 1

HCID 712699075,6-bis(Benzyloxy)-N-[(4-fluorophenyl)methyl]pyridazin-3-amine

시약·촉매·용매 2

HCID 53384307Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

3,4-Bis(benzyloxy)-6-chloropyridazine (Intermediate 1) (1 g, 3.1 mmol), [1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) dichloride (0.100 g, 0.15 mmol) and sodium tert-butoxide (0.59 g, 6.1 mmol) were added to dioxane (10.2 ml). The resulting mixture was purged with nitrogen before 4-fluorobenzylamine (78 mg, 6.1 mmol) was added. The mixture was heated at 120° C. for 1 hour under microwave irradiation. Upon cooling the crude mixture was quenched with water and extracted with ethyl acetate before the organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on silica eluting with 0-100% ethyl acetate/petrol to yield the title compound.

후처리

  1. additionwas added
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate before the organic extracts
  4. dry with materialwere dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica eluting with 0-100% ethyl acetate/petrol

출처 및 근거

ORD 기록
ord-9098af5f01ae4862a06b5c17d07a51ae
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290456B2

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