3-(3,6-Dihydro-2H-pyran-4-yl)-5-nitro-1-trityl-1H-indazole → 3-(3,6-dihydro-2H-pyran-4-yl)-1-trityl-1H-indazol-5-ylamine

HRID 1038059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038059
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=3)[N:9]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:8]=2)[CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[CH2:2][CH:3]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH2:16])[CH:14]=3)[N:9]([C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:8]=2)[CH2:5][CH2:6]1.[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH2:16])[CH:14]=3)[N:9]([C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:8]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 1

HCID 674194943-(3,6-Dihydro-2H-pyran-4-yl)-5-nitro-1-trityl-1H-indazole

Produkt 2

HCID 674191893-(3,6-dihydro-2H-pyran-4-yl)-1-trityl-1H-indazol-5-ylamineHCID 674211453-(tetrahydro-pyran-4-yl)-1-trityl-1H-indazol-5-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-(3,6-Dihydro-2H-pyran-4-yl)-5-nitro-1-trityl-1H-indazole (100 mg, 0.2 mmol) in methanol was added and Pd/C (10%, 20 mg). The reaction mixture was evacuated under vacuum and hydrogen gas was filled. After repeated three times the reaction was kept under hydrogen atmosphere overnight at room temperature. LCMS showed the starting material was consumed completely and both 3-(3,6-dihydro-2H-pyran-4-yl)-1-trityl-1H-indazol-5-ylamine and 3-(tetrahydro-pyran-4-yl)-1-trityl-1H-indazol-5-ylamine were obtained. The two products were separated using prep-HPLC to give both product in 60% and 40% yield respectively.

Aufarbeitung

  1. customThe reaction mixture was evacuated under vacuum and hydrogen gas
  2. additionwas filled
  3. customwas consumed completely

Quellen und Nachweise

ORD-Eintrag
ord-19c0a2dde73148eabefa60eb5540a332
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546404B2

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