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Trifluoroacetic acid → 2-(1-ethyl-4-methoxy-6-phenyl-1H-indol-3-yl)-N,N-dimethylethanamine

HRID 1404147
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1404147
[CH3:1][N:2]([CH3:25])[CH2:3][CH:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][C:13]=2[O:15][CH3:16])[N:8]([CH2:23][CH3:24])[CH:7]=1)O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:23]([N:8]1[C:9]2[C:14](=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)[C:6]([CH2:4][CH2:3][N:2]([CH3:25])[CH3:1])=[CH:7]1)[CH3:24]
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Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 583040302-(dimethylamino)-1-(1-ethyl-4-methoxy-6-phenyl-1H-indol-3-yl)ethanol

Produkt 1

HCID 509956292-(1-ethyl-4-methoxy-6-phenyl-1H-indol-3-yl)-N,N-dimethylethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

36-5 (68 mg, 0.2 mmol) was dissolved in DCM (2 mL) and triethylsilane (0.32 mL, 2.0 mmol) was added at 0° C. Trifluoroacetic acid (126 uL, 1.6 mmol) was added dropwise. After 20 minutes, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and then diluted with DCM. The organic layer was dried over MgSO4, filtered, and evaporated. The resulting residue was purified on silica gel column chromatography eluting with DCM/methanol (0-10%) containing 0.1% NH4OH to give the desired product. The product was acidified with HCl to afford 36-6 (19.6 mg, 27%) as an off-white solid. 1H NMR (300 MHz, D2O): δ (ppm) 7.62 (m, 2H), 7.42-7.24 (m, 4H), 7.06 (s, 1H), 6.78 (s, 1H), 4.04 (q, J=7.5 Hz, 2H), 3.88 (s, 3H), 3.31 (t, J=8.4 Hz, 2H), 3.12 (t, J=7.5 Hz, 2H), 2.76 (s, 6H), 1.24 (s, 7.5 Hz, 3H). LCMS: calc 322.4 and found: 323.1 [MH]+.

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. additiondiluted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified on silica gel column chromatography
  7. washeluting with DCM/methanol (0-10%)
  8. additioncontaining 0.1% NH4OH

Quellen und Nachweise

ORD-Eintrag
ord-d7bacca5d91e467e94a786789d7182f1
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08912220B2

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