Dimethylformamide → 2-(5-Methoxy-2-methyl-1h-indol-3-yl)acetamide

HRID 381400

Reaktionsgleichung

Reaktionsgleichung von HRID 381400
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([OH:16])=O.CC[N:19]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl-].[NH4+].CN(C=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH2:13][C:14]([NH2:19])=[O:16]

Komponenten

8

Edukt 6

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 2441462-(5-Methoxy-2-methyl-1h-indol-3-yl)acetamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A reaction mixture containing Compound 1 (880 mg, 4.02 mmol), EDCl (1.16 g,6.04 mmol), HOBt (816 mg,6.04 mmol), DIPEA (2.8 mL, 16.08 mmol), ammonium chloride (430 mg, 8.04 mmol) in anhydrous DMF 16 mL (4 mL DMF/1 mmol) was stirred at rt for 5 hours. The reaction was diluted with water and extracted with EtOAc (3×10 mL). The combined EtOAc extracts were washed with saturated NaHCO3 (2×10 mL), water, dried (MgSO4), filtered, and the solvent concentrated in vacuo till a minimum volume of EtOAc remained. Upon cooling, the desired primary amide crystallized out as a white crystalline solid, in 64% yield. mp=146-148° C. t is noted that Shaw, “The Synthesis of Tryptamines Related to Seratonin”, Vol. 77, J. Amer. Chem. Soc., pp. 4319-4324 (1955) reported the mp=147-150° C. 1H NMR (DMSO-d6) δ 10.56 (s, 1 H, NH), 7.34 (bs, 1 H, CONH), 6.96-7.22 (m, 1 H, ArH), 6.81 (s, 1 H, ArH), 6.74 (bs, 1 H, CONH), 6.58-6.62 (m, 1 H, ArH), 3.78 (s, 3 H, CH3), 3.34 (s, 2 H, CH2), 2.29 (s, 3 H, CH3). ESI-CID 219 (MH+), m/z 187, 174, 148.

Aufarbeitung

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined EtOAc extracts were washed with saturated NaHCO3 (2×10 mL), water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe solvent concentrated in vacuo till a minimum volume of EtOAc
  6. temperatureUpon cooling
  7. customthe desired primary amide crystallized out as a white crystalline solid, in 64% yield
  8. customThe Synthesis of Tryptamines

Quellen und Nachweise

ORD-Eintrag
ord-9cda3f52a85642a796926de967d07843
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306890B1

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