Methanol → 6-(4-chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine

HRID 2401373ノート

反応式

HRID 2401373 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15](F)=[N:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:20]([CH3:23])=[N:21][O:22][C:11]=3[CH2:10][N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:26][OH:27]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([O:27][CH3:26])=[N:16][CH:17]=[CH:18][C:13]=3[C:12]3[C:20]([CH3:23])=[N:21][O:22][C:11]=3[CH2:10][N:9]=2)=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 573445176-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepine

生成物 1

HCID 573445186-(4-chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine

実験手順

To a solution of 6-(4-chlorophenyl)-7-fluoro-1-methyl-4H-isoxazolo[4,5-e]pyrido[3,4-c]azepine (0.030 g, 0.092 mmol) in MeOH (2 mL) was added sodium hydride (60% dispersed in mineral oil) (0.037 g, 0.915 mmol) at room temperature. The reaction was stirred at room temperature for 15 min (or until the gas evolution stopped) before it was heated to 80° C. for 75 min in a sealed vial. The reaction was then concentrated to dryness under vacuum, and the residue was purified by flash chromatography (hexane/EtOAc 19:1 to 5:5) to give 6-(4-chlorophenyl)-7-methoxy-1-methyl-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepine as a white solid (0.031 g). 1H NMR (400 MHz, DMSO-d6) δ 8.42 (d, J=5.49 Hz, 1H), 7.43 (d, J=5.26 Hz, 1H), 7.39 (td, J=2.10, 8.70 Hz, 2H), 7.26 (td, J=2.10, 8.47 Hz, 2H), 5.24 (d, J=13.28 Hz, 1H), 4.11 (d, J=13.50 Hz, 1H), 3.61 (s, 3H), 2.55 (s, 3H); LC/MS m/z 340 [M+H]+.

後処理

  1. temperaturewas heated to 80° C. for 75 min in a sealed vial
  2. concentrationThe reaction was then concentrated to dryness under vacuum
  3. customthe residue was purified by flash chromatography (hexane/EtOAc 19:1 to 5:5)

出典と根拠

ORDレコード
ord-1538b7803fc645b39742972390e2e33a
出典データセット
uspto-grants-2014_08
特許番号
US08796261B2

反応ノート

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