Hydrochloric Acid → 2-[(1-Methyl-1H-indazol-5-yl)oxy]-3-pyridinemethanamine

HRID 909142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909142
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[N:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]#[N:15])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Cl>CO.[OH-].[OH-].[Pd+2]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[C:13]([CH2:14][NH2:15])=[CH:16][CH:17]=[CH:18][N:19]=3)=[CH:8][CH:9]=2)[CH:4]=[N:3]1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 574187422-(1-Methyl-1H-indazol-5-yloxy)-nicotinonitrile

Produkt 1

HCID 674103932-[(1-Methyl-1H-indazol-5-yl)oxy]-3-pyridinemethanamineAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

2-(1-Methyl-1H-indazol-5-yloxy)-nicotinonitrile (3n) (0.132 g, 0.528 mmol) was suspended in MeOH (6 mL). Pd(OH)2 (0.060 mg, 0.427 mmol) was added under a nitrogen atmosphere followed by concentrated aqueous HCl (0.6 mL). The system was purged with H2 gas and the reaction stirred at room temperature for 3 hours under an H2(g) atmosphere. The reaction mixture was filtered through a pad of celite, washed through with MeOH. The organics were concentrated under reduced pressure to afford the crude product, which was purified by flash column chromatography (MeOH/Et3N/EtOAc) to provide the desired product (4n) (0.047 g, 35% yield). 1H NMR (400 mHz, CD3OD) δ 7.96 (s, 1H), 7.90 (d, J=4.7 Hz, 1H), 7.82 (d, J=7.0 Hz, 1H), 7.56 (d, J=9.4 Hz, 1H), 7.46 (d, J=2.3 Hz, 1H), 7.23-7.21 (m, 1H), 7.09-7.06 (m, 1H), 4.07 (s, 3H), 3.95 (s, 2H).

Aufarbeitung

  1. customThe system was purged with H2 gas
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washwashed through with MeOH
  4. concentrationThe organics were concentrated under reduced pressure
  5. customto afford the crude product, which
  6. customwas purified by flash column chromatography (MeOH/Et3N/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-f29e935fe0494a018460d15d51b9ad30
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017641B2

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