Sodium cyanoborohydride → 5-(6-Chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole

HRID 2264586

反応式

HRID 2264586 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[CH:12]3)[CH:3]=1.[BH3-]C#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH2:13][CH2:12]3)[CH:3]=1

参加物

4

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 574551565-((6-Chloropyrimidin-4-yl)oxy)-1H-indole

生成物 1

HCID 858916285-(6-Chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 246 mg (1.0 mMol) of 5-(6-chloro-pyrimidin-4-yloxy)-1H-indole (WO 03/099771; Stage 163.1) in 5.5 ml acetic acid is cooled to 10-15° C. Then 314 mg (5 mMol) NaBH3CN are added portionwise. After 1 h stirring, 9 g of ice are added and the mixture is concentrated partially in vacuo. The residue is dissolved in 25 ml 1 N NaOH and extracted three times with EtOAc. The organic layers are washed twice with water and brine, dried (Na2SO4) and concentrated at rt in vacuo: MS: [M+1]+=248; TLC(EtOAc/hexane 1:1): Rf=0.31.

後処理

  1. concentrationthe mixture is concentrated partially in vacuo
  2. dissolutionThe residue is dissolved in 25 ml 1 N NaOH
  3. extractionextracted three times with EtOAc
  4. washThe organic layers are washed twice with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated at rt in vacuo

出典と根拠

ORDレコード
ord-87a0ceb01dc54bf09ee1d6020920e641
出典データセット
uspto-grants-2010_12
特許番号
US07855215B2

関連ノート

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