Water → (4-Chlorophenyl)-[4-(hydroxypyridin-4-yl-methyl)-1-methyl-1H-pyrrol-2-yl]-methanone

HRID 2182817

Reaktionsgleichung

Reaktionsgleichung von HRID 2182817
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([Li])CCC.[Cl:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([C:20]2[N:24]([CH3:25])[CH:23]=[C:22]([CH:26]=[O:27])[CH:21]=2)=[O:19])=[CH:16][CH:15]=1.O>CCOCC.CCCCCC.C1COCC1>[Cl:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([C:20]2[N:24]([CH3:25])[CH:23]=[C:22]([CH:26]([OH:27])[C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[CH:21]=2)=[O:19])=[CH:16][CH:15]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 142684-BromopyridineHCID 224810525-(4-Chlorobenzoyl)-1-methyl-1H-pyrrole-3-carboxaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 10308647(4-Chlorophenyl)-[4-(hydroxypyridin-4-yl-methyl)-1-methyl-1H-pyrrol-2-yl]-methanoneAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 1.36 g (8.64 mmol) of 4-bromopyridine in 12 mL of ether was cooled to −40° C. under argon and 5.4 mL (8.64 mmol) of 1.6 M n-butyllithium in hexane was added dropwise. A solution of 1.07 g (4.3 mmol) of 5-(4-chloro-benzoyl)-1-methyl-1H-pyrrole-3-carboxaldehyde (obtained from Procedure 5) in 15 mL of THF was added dropwise (exotherm). The reaction was stirred for 5 min and poured into water and extracted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated. The residue was flash chromatographed (50%acetone/hexane). The trailing spot was concentrated and recrystallized from EtOAc to give 0.74 g (52% yield) of the title compound as a white solid: mp 145-146° C. ES-MS m/z=327 (M++H). 1H NMR (300 MHz, CDCl3) δ 2.55 (s, 1H); 4.0 (s, 3H); 5.8 (s, 1H); 6.56 (s, 1H); 6.8 (s, 1H); 7.3 (dd, 2H); 7.4 (dd, 2H); 7.75 (dd, 2H); 8.55 (dd, 2H). Anal calc'd for C18H15ClN2O2: 66.16; H, 4.63; N, 8.57. Found: C, 65.8; H, 4.65; N, 8.63.

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customchromatographed (50%acetone/hexane)
  5. concentrationThe trailing spot was concentrated
  6. customrecrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-bc5cbdd3b39546738068e47c8b318ec2
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897319B2

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