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

HRID 2264586

Reaktionsgleichung

Reaktionsgleichung von HRID 2264586
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-87a0ceb01dc54bf09ee1d6020920e641
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855215B2

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