Water → HCID 118275229, Verbindung

HRID 526009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526009
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][C:9]([C:11](=[O:28])[NH:12][CH:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:14]([F:17])([F:16])[F:15])=[CH:10][C:5]2=[CH:4][C:3]=1[C:29]([O:31][CH3:32])=[O:30].[H-].[Na+].I[CH2:36][CH3:37].O>CN(C)C=O.C(OCC)(=O)C>[CH2:36]([N:8]1[C:6]2=[N:7][C:2]([CH3:1])=[C:3]([C:29]([O:31][CH3:32])=[O:30])[CH:4]=[C:5]2[CH:10]=[C:9]1[C:11](=[O:28])[NH:12][CH:13]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)[C:14]([F:15])([F:16])[F:17])[CH3:37]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 90039588HCID 90039588, Verbindung

Produkt 1

HCID 118275229HCID 118275229, VerbindungAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.58 g, 3.44 mmol) was dissolved under argon at 0° C. in N,N-dimethylformamide (35 ml). Sodium hydride (60%; 0.165 g, 4.12 mmol) was added and the mixture was stirred with ice cooling for 2 h. Iodoethane (0.643 g, 4.12 mmol) was added and the reaction mixture was thawed with stirring over 18 h. Water and ethyl acetate were added and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulphate, and the solvent was removed under reduced pressure. The residue was chromatographed with cyclohexane/ethyl acetate (3/1) and gave 1.15 g (66% of theory) of methyl 1-ethyl-6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate. HPLC-MS: log P=6.27; mass (m/z): 488.1 (M+H)+; 1HNMR (D6-DMSO): δ 1.20 (t, 3H), 2.83 (s, 3H), 3.87 (s, 3H), 4.59 (q, 2H), 6.30-6.34 (m, 1H), 7.42 (s, 1H), 7.70-7.84 (m, 2H), 8.06 (d, 1H), 7.93-7.97 (m, 1H), 8.21 (s, 1H), 8.67 (s, 1H).

Aufarbeitung

  1. stirringwith stirring over 18 h
  2. customthe phases were separated
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was chromatographed with cyclohexane/ethyl acetate (3/1)

Quellen und Nachweise

ORD-Eintrag
ord-c8a7ec36a09e4bb1ac12e657ac241002
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345247B2

Notizen zur Reaktion

Wird geladen…