Dichloromethane → 5,6-Dimethoxyindoline

HRID 624014

Reaktionsgleichung

Reaktionsgleichung von HRID 624014
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+].C(Cl)Cl>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][CH2:7][CH2:6]2

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 844315,6-DimethoxyindoleHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 110629785,6-Dimethoxyindoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 5,6-dimethoxyindole (2.00 g, 11.29 mmol) in acetic acid (120 mL), sodium cyanoborohydride (2.13 g, 33.86 mmol) was added in portions (slightly exothermic). After stirring at rt for 1 h, DCM was added and the org. layer was washed with sat. NaHCO3-solution and brine. The org. layer was dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield 5,6-dimethoxyindoline as a brown solid, which was stored in the freezer until it was used in step 4. LC-MS conditions B: tR=0.28 min, [M+H]+=180.23.

Aufarbeitung

  1. washlayer was washed with sat. NaHCO3-solution and brine
  2. dry with materiallayer was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ebc0c9f7b9be406fbe4a1de9f40e0cb0
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303023B2

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