1-Methylcyclohexane-1-carboxaldehyde → (1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanol

HRID 1677382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677382
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[N:4]([Si](C(C)C)(C(C)C)C(C)C)[CH:3]=1.C([Mg]Cl)(C)C.[Li+].[Cl-].[CH3:40][C:41]1([CH:47]=[O:48])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>O1CCCC1>[CH3:40][C:41]1([CH:47]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=4)[N:9]=3)[NH:4][CH:3]=2)[OH:48])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1

Komponenten

5

Edukt 3

HCID 111371681-Methylcyclohexane-1-carboxaldehydeHCID 595405257-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazineHCID 178461733HCID 178461733, Verbindung

Produkt 1

HCID 59540707(1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanolAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 7-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (247 mg, 0.435 mmol) in anhydrous tetrahydrofuran (5 ml) was cooled to −78° C. and treated with iPrMgCl—LiCl (1M in tetrahydrofuran, 0.87 ml, 0.87 mmol) dropwise. The reaction mixture was allowed to stir for 20 minutes, and then 1-methyl-cyclohexanecarbaldehyde (219 mg, 1.74 mmol) was added rapidly. The reaction mixture was allowed to stir at −78° C. for 1 hour and then room temperature for 1 hour. The reaction mixture was partitioned between EtOAc/saturated aqueous. NH4Cl. The organic layers were collected, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography using 15-100% EtOAc in hexanes as eluant to provide 81 mg (45%) of (1-methyl-cyclohexyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanol as a pale yellow solid. M+H=412.

Aufarbeitung

  1. stirringto stir at −78° C. for 1 hour
  2. waitroom temperature for 1 hour
  3. customThe reaction mixture was partitioned between EtOAc/saturated aqueous
  4. customThe organic layers were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-93ac8c2e43d14235a5e73b9db74e3916
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008298B2

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