4-Fluorobenzaldehyde → HCID 58531372、化合物

HRID 1889703ノート

反応式

HRID 1889703 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=2)=[CH:5][CH:4]=1.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CC(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH:16][CH2:22][C:21]3[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=3)[CH:10]=2)=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 179988493-(Aminomethyl)-4'-chlorobiphenyl hydrochloride

生成物 1

HCID 58531372HCID 58531372、化合物収率 81.9%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (4′-chlorobiphenyl-3-yl)methanamine HCl salt (Chem-Impex International, Inc., 0.6 g, 2.36 mmol) in CH2Cl2 (6 mL) and 2-propanol (6.00 mL) was added 4-fluorobenzaldehyde (0.28 mL, 2.60 mmol). The resulting reaction mixture was stirred at rt for 1 h. and sodium triacetoxyborohydride (0.75 g, 3.54 mmol) was added under N2. After stirring at rt for 3 h, the reaction mixture was quenched with saturated aqueous NaHCO3, stirred for 10 minutes and concentrated in vacuo. The residue was diluted with ethyl acetate and saturated aqueous NaHCO3 solution. The organic layer was separated, washed with brine, dried over MgSO4, filtered and the filtrate solution was concentrated in vacuo. The residue was purified by flash silica gel chromatography eluting with 0-10% ethyl acetate in CH2Cl2 to afford the desired compound (0.63 g, 73%) as a colorless oil. 1H NMR (CDCl3) δ 7.62-7.41 (m, 6H), 7.37-7.32 (m, 3H), 7.09-7.01 (m, 3H), 3.92 (s, 2H), 3.83 (s, 2H). MS (ESI): 326.0 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. stirringAfter stirring at rt for 3 h
  3. customthe reaction mixture was quenched with saturated aqueous NaHCO3
  4. stirringstirred for 10 minutes
  5. concentrationconcentrated in vacuo
  6. additionThe residue was diluted with ethyl acetate and saturated aqueous NaHCO3 solution
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationthe filtrate solution was concentrated in vacuo
  12. customThe residue was purified by flash silica gel chromatography
  13. washeluting with 0-10% ethyl acetate in CH2Cl2

出典と根拠

ORDレコード
ord-b8910cac4bf747a8a95fc6ce6a837f66
出典データセット
uspto-grants-2013_08
特許番号
US08501992B2

反応ノート

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