Triphenylphosphine → Methyl 3-amino-1-[(5-chloro-1-isobutyl-indazol-7-yl)methyl]indazole-5-carboxylate

HRID 2203183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2203183
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11]O)[CH:10]=1)[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:6]=[CH:5]2.[NH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=2)[NH:20][N:19]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=2)[N:20]([CH2:11][C:9]2[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:8]=2[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:6]=[CH:5]3)[N:19]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 84663082methyl 3-amino-1H-indazole-5-carboxylateHCID 118251601(5-Chloro-1-isobutyl-1H-indazole-7-yl)-methanol

Produkt 1

HCID 118251621Methyl 3-amino-1-[(5-chloro-1-isobutyl-indazol-7-yl)methyl]indazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of compound 17 (0.112 g, 0.47 mmol), methyl 3-amino-1H-indazole-5-carboxylate (0.075 g, 0.39 mmol), di-tert-butyl azocarboxylate (0.135 g, 0.59 mmol), triphenylphosphine (0.155 g, 0.59 mmol), in tetrahydrofuran (4 mL) was heated at 140° C. under microwave conditions for 20 minutes. Then, the reaction was quenched by adding water and diluted with ethyl acetate. The organic layer was separated, washed with Brine, dried (MgSO4), filtered and the solvent was evaporated. Then, the residue was purified by chromatography column on a 20 g SPE cartridge to give the title compound as a colorless solid. (0.090 g, 56%)

Aufarbeitung

  1. customThen, the reaction was quenched
  2. additionby adding water
  3. additiondiluted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with Brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThen, the residue was purified by chromatography column on a 20 g SPE cartridge

Quellen und Nachweise

ORD-Eintrag
ord-bd7ee3c4db5f4da1adfc5cffe29b15aa
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365569B2

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