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1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine → [1-(2-{[tert-butyl(methyl)silyl]oxyl}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl](4-chloropyridin-2-yl)methanone

HRID 1753054
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1753054
[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:15](I)=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])(C)[CH3:2].C([Mg]Cl)(C)C.[Cl:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([C:35](NOC)=[O:36])[C:30]=1C>C1COCC1>[C:4]([SiH:1]([CH3:2])[O:8][CH2:9][C:10]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:15]([C:35]([C:31]2[CH:30]=[C:29]([Cl:28])[CH:34]=[CH:33][N:32]=2)=[O:36])=[CH:14]1)([CH3:11])[CH3:12])([CH3:5])([CH3:6])[CH3:7]
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Komponenten

5

Edukt 3

HCID 900934361-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridineHCID 900937914-chloro-N-methoxy-M-methylpicolinamideHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 137331321[1-(2-{[tert-butyl(methyl)silyl]oxyl}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl](4-chloropyridin-2-yl)methanoneAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine (Preparation 65, 3.99 g, 9.06 mmol) was dissolved in THF (75 mL) and the solution was degassed and cooled to −5° C. 2M iPrMgCl in THF (5.44 mL, 10.9 mmol) was added dropwise and the resulting yellow solution stirred at this temperature for 45 minutes. A solution of 4-chloro-N-methoxy-M-methylpicolinamide (2.18 g, 10.9 mmol) in THF (20 mL) was added dropwise and the reaction allowed to warm to room temperature for 4.5 hours. The reaction was partitioned between saturated aqueous ammonium chloride solution (30 mL) and EtOAc (50 mL), the organic layer was collected, dried and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-90% EtOAc in DCM to afford the title compound as an orange oil (2.37 g, 59%). Taken on to the next step directly.

Aufarbeitung

  1. customthe solution was degassed
  2. temperatureto warm to room temperature for 4.5 hours
  3. customThe reaction was partitioned between saturated aqueous ammonium chloride solution (30 mL) and EtOAc (50 mL)
  4. customthe organic layer was collected
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with 0-90% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-b20284d6cfa7497f97132974f2aeadcc
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09163021B2

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