Sodium Chlorite → 1H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(1,1-dimethylethyl)dimethylsilyl]-

HRID 1994196Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1994196
[C:1]([Si:5]([CH3:18])([CH3:17])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([CH:15]=[O:16])[CH:14]=[C:9]2[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].[O-:19]Cl=O.[Na+]>C(O)(C)(C)C.CC(=CC)C.O>[C:1]([Si:5]([CH3:18])([CH3:17])[N:6]1[C:10]2=[N:11][CH:12]=[C:13]([C:15]([OH:19])=[O:16])[CH:14]=[C:9]2[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 2

HCID 23668197Sodium ChloriteHCID 497590381H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 1-[(1,1-dimethylethyl)dimethylsilyl]-

Produkt 1

HCID 497588951H-Pyrrolo[2,3-B]pyridine-5-carboxylic acid, 1-[(1,1-dimethylethyl)dimethylsilyl]-Ausbeute 16,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 105532-Methyl-2-buteneLösungsmittel

Versuchsvorschrift

To a stirred and cooled (0° C.) solution of aldehyde 16 (115 mg, 0.44 mmol) in tert-butanol (3.1 mL) and 2-methyl-2-butene (0.77 mL) was added a solution of NaClO2 (194 mg, 2.1 mmol) and NaH2PO4.H2O (244 mg, 1.8 mmol) in water (2.31 mL) dropwise. When 16 was consumed (TLC) the mixture was partitioned between AcOEt and water. The organic layer was washed with saturated brine (1×), dried (MgSO4), filtered and concentrated to afford acid 11 (20 mg, 16%) as an off-white solid. 1H NMR (400 MHz; CDCl3) δ 0.66 (s, 6H), 0.94 (s, 9H), 6.65 (s, 1H), 7.32 (s, 1H), 8.61 (s, 1H) and 9.03 (s, 1H).

Aufarbeitung

  1. customWhen 16 was consumed (TLC) the mixture
  2. customwas partitioned between AcOEt and water
  3. washThe organic layer was washed with saturated brine (1×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0b3dd40dc51649ba930d40f1ea995cc8
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652137B2

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