Triacetoxyperiodinane → (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone

HRID 1854490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1854490
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([CH:36]([C:38]2[C:43]([Cl:44])=[CH:42][N:41]=[C:40]3[N:45]([Si:48]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[CH:49]([CH3:51])[CH3:50])[CH:46]=[CH:47][C:39]=23)[OH:37])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([C:38]2[C:43]([Cl:44])=[CH:42][N:41]=[C:40]3[N:45]([Si:48]([CH:52]([CH3:54])[CH3:53])([CH:55]([CH3:57])[CH3:56])[CH:49]([CH3:50])[CH3:51])[CH:46]=[CH:47][C:39]=23)=[O:37])[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 58010130(1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol

Produkt 1

HCID 58010051(1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanoneAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dess-Martin periodinane (14.63 g, 34.5 mmol) was added to a solution of (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol (5.89 g, 11.5 mmol) in DCM (120 mL) at about 0° C. and the resulting mixture was stirred for about 16 h while warming to ambient temperature. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous NaHCO3 (150 mL) and EtOAc (200 mL). The organic phase was washed with brine (120 mL) and concentrated under reduced pressure. Purification by silica gel chromatography eluting first with heptane (IL) and then with 1:7 EtOAc:heptane (1 L) yielded (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone (1.45 g, 25%) as a yellow oil: LC/MS (Table 2, Method a) Rt=3.24 min; MS m/z: 511 (M+H)+

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between saturated aqueous NaHCO3 (150 mL) and EtOAc (200 mL)
  3. washThe organic phase was washed with brine (120 mL)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel chromatography
  6. washeluting first with heptane (IL)

Quellen und Nachweise

ORD-Eintrag
ord-db464d88cc714fb4b246807440dd7c98
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962629B2

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