Lithium borohydride → HCID 86301335, Verbindung

HRID 1748389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748389
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([CH:18]([OH:20])[CH3:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 4148881Lithium borohydrideHCID 4311764Sodium borohydride2×HCID 86301334HCID 86301334, Verbindung

Produkt 1

HCID 86301335HCID 86301335, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled solution, 0° C., of 1-(7-((4-fluorobenzyl)oxy)quinolin-3-yl)ethanone (Example 42, 53 mg, 0.18 mmol) in THF was added NaBH4 (8 mg, 0.24 mmol). The reaction mixture was stirred for 1 hour. A further portion of NaBH4 (20 mg, 0.59 mmol) was added and stirred for 30 minutes at 0° C. LiBH4 (50 mg, 2.30 mmol) was added and the reaction was stirred for 15 minutes before being quenched with sat. NH4Cl (aq.) solution. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and concentrated under reduced pressure onto silica. Purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound as a white solid (20 mg, 38%). 1H NMR (400 MHz, CDCl3) δ 8.85 (d, J=1.6 Hz, 1H), 8.10 (s, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.53-7.43 (m, 3H), 7.31-7.26 (m, 1H), 7.09 (t, J=8.6 Hz, 2H), 5.17 (s, 2H), 5.12 (q, J=6.5 Hz, 1H), 1.62 (d, J=6.7 Hz, 3H). [M+H]=298.3.

Aufarbeitung

  1. stirringstirred for 30 minutes at 0° C
  2. stirringthe reaction was stirred for 15 minutes
  3. custombefore being quenched with sat. NH4Cl (aq.) solution
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. concentrationconcentrated under reduced pressure onto silica
  7. customPurification (FCC, SiO2, 0-5%, MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-a3f613f9d86448b3bbd1a1da5f7be4ce
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150572B2

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