1-(3-fluorobenzyl)-5-nitro-1H-indazole → 1-(3-Fluorobenzyl)-1H-indazol-5-amine

HRID 222052

Reaktionsgleichung

Reaktionsgleichung von HRID 222052
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[N:8]=[CH:7]2)([O-])=O>C(O)(=O)C.CCOC(C)=O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[N:8]=[CH:7]2

Komponenten

5

Edukt 1

HCID 219664901-(3-fluorobenzyl)-5-nitro-1H-indazole

Produkt 1

HCID 71470731-(3-Fluorobenzyl)-1H-indazol-5-amineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-nitro-1-N-(3-fluorobenzyl)indazole (7.9 g, 29.1 mmol, 1 equiv) and iron (8.13 g, 145.6 mmol, 5 equiv) were mixed in 200 mL acetic acid and 50 mL EtOAc, and were stirred at rt for 36 h. The reaction mixture was filtered through a pad of Celite®. The filtrate was concentrated in vacuo to 10 mL volume. The contents were diluted with water (10 mL) and neutralized with saturated Na2CO3 solution. The solution was extracted with EtOAc (3×500 mL), the combined organic layers dried over MgSO4, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography eluting with hexanes/EtOAC (4:1 to 3:1) to give 5-amino-1-N-(3-fluorobenzyl)indazole (5.32 g, 76%) as a light brown solid. 1H-NMR (DMSO-d6) δ 7.72 (s, 1H), 7.22-7.36 (m, 2H), 6.87-7.05 (m, 3H), 6.70-6.77 (m, 2H), 5.48 (s, 2H), 4.78 (br s, 2H); LCMS RT=1.66 min; [M+H]+=242.2.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. concentrationThe filtrate was concentrated in vacuo to 10 mL volume
  3. additionThe contents were diluted with water (10 mL)
  4. extractionThe solution was extracted with EtOAc (3×500 mL)
  5. dry with materialthe combined organic layers dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude material was purified by column chromatography
  9. washeluting with hexanes/EtOAC (4:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-be7a5ae511a74c2ba7958be2a030c5b4
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207172B2

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