(Dimethyl sulfide)trihydroboron → HCID 90013834, Verbindung

HRID 2279156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279156
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][CH:23]=3)[N:19]=[C:18]3[N:32]([CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][O:37]4)[N:33]=[C:34]([CH3:35])[C:17]=23)=O)[CH2:10][C@H:9]1[CH2:42][C:43]([F:46])([F:45])[F:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.CSC>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:16]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:26][CH:27]=3)[N:19]=[C:18]3[N:32]([CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][O:37]4)[N:33]=[C:34]([CH3:35])[C:17]=23)[CH2:10][C@H:9]1[CH2:42][C:43]([F:45])([F:46])[F:44])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 90013835HCID 90013835, Verbindung

Produkt 1

HCID 90013834HCID 90013834, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 350 mg of [(R)-4-Benzyl-3-(2,2,2-trifluoro-ethyl)-piperazin-1-yl]-[6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone in 6 ml of dry THF 4.4 ml of borane-dimethylsulfide complex (1 M in DCM) was added slowly at r.t., and the reaction was heated to reflux for 6 h. The reaction was quenched by the addition of methanol, and the solvents were evaporated. The residue was purified by flash chromatography (silica, heptanes/ethyl acetate) yielding 217 mg (63%) of the title compound.

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 6 h
  3. customThe reaction was quenched by the addition of methanol
  4. customthe solvents were evaporated
  5. customThe residue was purified by flash chromatography (silica, heptanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e29acd58625f49cead0f6fcb9ac48c65
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133181B2

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