Cerium(III) chloride → 3-(2-(4-((1H-Benzo[D]imidazol-2-YL)(hydroxy)methyl)phenoxy)pyridin-3-YL)cyclopent-2-enol

HRID 1880162

反応式

HRID 1880162 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:30]=[CH:29][C:15]([O:16][C:17]2[C:22]([C:23]3[CH2:27][CH2:26][C:25](=[O:28])[CH:24]=3)=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:14][CH:13]=1)=[O:11].[Cl-].[Ce+3].[Cl-].[Cl-].[B-].[Na+]>O1CCCC1.CO>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:11])[C:12]1[CH:30]=[CH:29][C:15]([O:16][C:17]2[C:22]([C:23]3[CH2:27][CH2:26][CH:25]([OH:28])[CH:24]=3)=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 24636Cerium(III) chlorideHCID 22959485VertellusHCID 462148723-(2-(4-(1H-Benzo[D]imidazole-2-carbonyl)phenoxy)pyridin-3-YL)cyclopent-2-enone

生成物 1

HCID 593267903-(2-(4-((1H-Benzo[D]imidazol-2-YL)(hydroxy)methyl)phenoxy)pyridin-3-YL)cyclopent-2-enol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A suspension of 3-(2-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyridin-3-yl)cyclopent-2-enone (2125 mg, 5.37 mmol) and cerium (iii) chloride (1325 mg, 5.37 mmol) in tetrahydrofuran (300 mL) and methanol (30.0 mL) was cooled to 0° C. under nitrogen. Sodium borohydrate (813 mg, 21.50 mmol) was added in 4 lots over 20 min. The reaction was warmed to 23° C. over 2 h. After a total reaction time of 4 h, the reaction was quenched with saturated ammonium chloride solution (10 ml, slowly—effervescence). The solution was diluted with EtOAc (500 mL) and washed with saturated ammonium chloride solution (100 mL) and brine (100 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 1-8% methanol/dichloromethane), affording the product as a yellow film.

後処理

  1. temperatureThe reaction was warmed to 23° C. over 2 h
  2. customAfter a total reaction time of 4 h, the reaction was quenched with saturated ammonium chloride solution (10 ml
  3. additionThe solution was diluted with EtOAc (500 mL)
  4. washwashed with saturated ammonium chloride solution (100 mL) and brine (100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (eluant: 1-8% methanol/dichloromethane)
  8. customaffording the product as a yellow film

出典と根拠

ORDレコード
ord-6e6401a168784fb885653924ffc7afdb
出典データセット
uspto-grants-2012_11
特許番号
US08318718B2

関連ノート

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