Ethanol → racemic cis-2-[1-(4-Bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]cyclohexanecarboxylic acid

HRID 2178425ノート

反応式

HRID 2178425 の反応式
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)=[CH:10][C:9]=2[N+:26]([O-])=O)=[CH:4][CH:3]=1.[OH2:31].O.[Sn](Cl)Cl.[CH2:36]([OH:38])[CH3:37]>>[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:8]3[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]4[CH:25]=[CH:24][C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[N:17]=4)=[CH:10][C:9]=3[N:26]=[C:5]2[C@H:4]2[CH2:3][CH2:2][CH2:30][CH2:29][C@H:37]2[C:36]([OH:31])=[O:38])=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 90414040N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline

生成物 1

HCID 86281518racemic cis-2-[1-(4-Bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]cyclohexanecarboxylic acid収率 54%

反応条件

温度
80 °C

実験手順

To a 1 L round-bottomed flask were added a stir bar, N-(4-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline (6.1 g, 13 mmol), tin(II) chloride dihydrate (12.5 g, 55.4 mmol) and ethanol (250 mL). The resulting mixture was heated to 80° C. After 24 h, the mixture was cooled and partitioned between water (100 mL) and EtOAc (300 mL). The mixture was stirred vigorously while the pH was adjusted to 8 using 2 M sodium carbonate. The organic layer was separated and washed with brine (100 mL), dried with magnesium sulfate, filtered, and concentrated to dryness to afford the title compound (3.1 mg, 54%). The residue was kept under vacuum until use.

後処理

  1. additionTo a 1 L round-bottomed flask were added a stir bar
  2. temperaturethe mixture was cooled
  3. custompartitioned between water (100 mL) and EtOAc (300 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (100 mL)
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-fe1aae63ecdc49aeafb9412b03e2e726
出典データセット
uspto-grants-2015_06
特許番号
US09067917B2

反応ノート

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