Hydrochloric Acid → 1-benzyl-4-(4-chlorophenyl)-5-(hydroxymethyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

HRID 1473184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473184
[CH2:1]([N:8]1[C:12]2[C:13](=[O:29])[N:14]([CH3:28])[C:15]([C:24](OC)=[O:25])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[BH4-].Cl>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:12]2[C:13](=[O:29])[N:14]([CH3:28])[C:15]([CH2:24][OH:25])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydride2×HCID 89462830methyl 1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

Produkt 1

HCID 894626421-benzyl-4-(4-chlorophenyl)-5-(hydroxymethyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-oneAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of methyl 1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (6.4 g, 15.7 mmol) in Toluene (80 mL) was treated with LiBH4 (3.43 g, 157 mmol) and then heated at 90° C. overnight. Additional LiBH4 (3.43 g, 157 mmol) was added and the mixture was allowed to stir for an additional 5 hours at 90° C. The mixture was cooled to 0° C., treated with HCl (1M) until pH<2 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-100% ethyl acetate/hexanes) to afford 1-benzyl-4-(4-chlorophenyl)-5-(hydroxymethyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (4.0 g, 10.6 mmol, 67% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) ppm 7.53-7.57 (m, 2H) 7.43-7.47 (m, 4H) 7.28-7.35 (m, 4H) 5.92-5.96 (m, 1H) 5.80 (s, 2H) 5.31 (s, 1H) 4.29-4.37 (m, 2H) 3.70 (s, 3H); LCMS (m/z) ES+=379 (M+1).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (0-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bf97ab1091384bcfa519caf88c717bed
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012642B2

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