Sodium triacetoxyborohydride → 2-(4-(1,1-Dimethylethyl)phenyl)-8-((1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)amino)-1(2H)-phthalazinone

HRID 133107

Reaktionsgleichung

Reaktionsgleichung von HRID 133107
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)[N:8]=[CH:7]2.[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C:25]([CH:32]=O)=[CH:24]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:20][C:19]([C:16]1[CH:15]=[CH:14][C:13]([N:9]2[N:8]=[CH:7][C:6]3[C:11](=[C:2]([NH:1][CH2:32][C:25]4[C:26]5[C:27](=[N:28][CH:29]=[CH:30][CH:31]=5)[NH:23][CH:24]=4)[CH:3]=[CH:4][CH:5]=3)[C:10]2=[O:12])=[CH:18][CH:17]=1)([CH3:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 691606278-amino-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one

Produkt 1

HCID 116259932-(4-(1,1-Dimethylethyl)phenyl)-8-((1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)amino)-1(2H)-phthalazinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 8-amino-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one (Example 1, Step E, 0.36 g, 1.1 mmol, 1 eq) and CH2Cl2 (50 mL) was added 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (0.16 g, 1.1 mmol, 1 eq) and NaBH(OAc)3 (0.72 g, 3.4 mmol, 3.0 eq). The reaction was stirred at RT for 12 h then quenched with H2O and extracted with CH2Cl2. The organic layer was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by silica flash chromatography (10-75% EtOAc:hexane) to give the desired product as a yellow solid. MS m/e 424 (M+H)+. Calc'd for C26H25N5O-423.51.

Aufarbeitung

  1. customthen quenched with H2O
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica flash chromatography (10-75% EtOAc:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-27cc4fb6d8be4f56838139a945ac0d5d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390820B2

Verknüpfte Notizen

Wird geladen…