Pyridine → (E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl) phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carbonitrile

HRID 390173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390173
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][N:15]1[C:42]2[C:37](=[CH:38][C:39]([C:43]([NH2:45])=O)=[CH:40][CH:41]=2)[C:17]2([CH2:22][CH2:21][N:20]([C:23](=[O:36])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])[CH2:19][CH2:18]2)[C:16]1=[O:46].N1C=CC=CC=1>O1CCOCC1.O>[CH3:14][N:15]1[C:42]2[C:37](=[CH:38][C:39]([C:43]#[N:45])=[CH:40][CH:41]=2)[C:17]2([CH2:22][CH2:21][N:20]([C:23](=[O:36])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:33])[F:34])[CH2:19][CH2:18]2)[C:16]1=[O:46]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 58295665(E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxamide

Produkt 1

HCID 58295783(E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl) phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of trifluoroacetic anhydride (34 mg, 0.157 mmol) in dioxane (4 mL) was added dropwise to a stirred, ice-cooled solution of (E)-1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carboxamide (60 mg, 0.131 mmol) and pyridine (60 mg, 0.262 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to afford the crude product. After purification by preparative HPLC, (E)-1-methyl-2-oxo-1′-(3-(2-(trifluoromethyl) phenyl)acryloyl)spiro[indoline-3,4′-piperidine]-5-carbonitrile was obtained (2.04 mg, 4%). 1H NMR: (400 MHz, CDCl3): δ=1.85 (m, 4H), 3.20 (m, 3H), 3.80-3.90 (m, 2H), 4.10 (m, 1H), 4.35 (m, 1H), 6.75 (m, 1H), 6.85 (m, 1H), 7.40 (m, 2H), 7.50 (m, 1H), 7.55 (m, 1H) 7.65 (m, 2H), 7.90 (m, 1H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customto afford the crude product
  5. customAfter purification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f008275bae6041bbba3df741e83643dc
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383629B2

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