3-Fluoro-4-methoxyaniline → HCID 59781130, Verbindung

HRID 606142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606142
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Br:11][C:12]1[CH:13]=[N:14][C:15](Cl)=[C:16]([CH:26]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]>C(O)CC(C)C.BrC1C=NC(Cl)=C(C=1)C(NC1C=CC=CC=1)=O>[Br:11][C:12]1[CH:13]=[N:14][C:15]([NH:10][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=2)=[C:16]([CH:26]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]

Komponenten

5

Edukt 2

HCID 5811103-Fluoro-4-methoxyaniline3×HCID 597811365-bromo-2-chloro-N-phenylnicotinamide2×

Produkt 1

HCID 59781130HCID 59781130, VerbindungAusbeute 373,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 597811365-bromo-2-chloro-N-phenylnicotinamideKatalysatorHCID 31260Isoamyl AlcoholLösungsmittel3×

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

5-bromo-2-chloro-N-phenylnicotinamide (224 mg, 719 μmol) and 3-fluoro-4-methoxybenzenamine (316.7 mg, 2244 μmol) were suspended in isoamyl alcohol (1.5 ml) in a reaction microwave vessel which was sealed. This vessel was heated in the Biotage Initiator microwave at 200° C. for 20 minutes, with 45 seconds of stirring beforehand, and then cooled to room temperature. This process was repeated using 5-bromo-2-chloro-N-phenylnicotinamide (810 mg, 2.60 mmol) and 3-fluoro-4-methoxybenzenamine (1.092 g, 7.74 mmol), and isoamyl alcohol (7.5 ml), and then repeated a third time with 5-bromo-2-chloro-N-phenylnicotinamide (1.643 g, 5.28 mmol), 3-fluoro-4-methoxybenzenamine (2.285 g, 16 mmol), and isoamyl alcohol (10 ml). These three sets of reaction were combined, concentrated, treated with Et2O, and filtered. The solid was washed with Et2O, and the filtrate was concentrated and purified on a silica gel filter (˜3 inches, DCM) to afford the desired 5-bromo-2-(3-fluoro-4-methoxyphenylamino)-N-phenylnicotinamide (3.49 g, 8.39 mmol, 75% yield). MS (ESI pos. ion) m/z: 416 (MH+, 79Br), 418 (MH+, 81Br). Calc'd exact mass for C19H15BrFN3O2: 415 (79Br), 417 (81Br).

Aufarbeitung

  1. customwhich was sealed
  2. temperaturecooled to room temperature
  3. customThese three sets of reaction
  4. concentrationconcentrated
  5. additiontreated with Et2O
  6. filtrationfiltered
  7. washThe solid was washed with Et2O
  8. concentrationthe filtrate was concentrated
  9. custompurified on a silica gel
  10. filtrationfilter (˜3 inches, DCM)

Quellen und Nachweise

ORD-Eintrag
ord-8b807acf389247318c87775e1f0deec9
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915287B2

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