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

HRID 2264586

반응식

HRID 2264586 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87a0ceb01dc54bf09ee1d6020920e641
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855215B2

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