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

HRID 927096

反応式

HRID 927096 の反応式
[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

参加物

6

反応物 3

HCID 673264-FluorobenzylamineHCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2 回HCID 23676156Sodium t-butoxide

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9098af5f01ae4862a06b5c17d07a51ae
出典データセット
uspto-grants-2016_03
特許番号
US09290456B2

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