Triethylamine → 2,2-Dimethyl-propionic acid 1H-indazol-6-yl Ester

HRID 967709

Reaktionsgleichung

Reaktionsgleichung von HRID 967709
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:10])[CH:8]=2)[CH:3]=[N:2]1.C(N(CC)CC)C.[CH3:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21]>ClCCl.CN(C1C=CN=CC=1)C.[Cl-].[NH4+]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:10][C:20](=[O:21])[C:19]([CH3:24])([CH3:23])[CH3:18])[CH:8]=2)[CH:3]=[N:2]1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 1354839876-hydroxy-1H-indazole

Produkt 1

HCID 697525662,2-Dimethyl-propionic acid 1H-indazol-6-yl EsterAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 1H-indazol-6-ol (0.88 g, 6.6 mmol) in dichloromethane (10 ml) at room temperature was added triethylamine (0.98 ml, 7.0 mmol) and DMAP (0.05 g) followed by trimethylacetyl chloride (0.82 ml, 6.6 mmol). After stirring for 1 h, the mixture was diluted with saturated aqueous solution of ammonium chloride (20 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with brine (10 ml), dried (MgSO4), and evaporated to a residue which was purified by chromatography (silica, 10% to 20% ethyl acetate in hexane) to give an oil (1.1 g, 76%): 1H NMR (CDCl3) δ 8.15 (d, J=0.8 Hz, 1H), 8.01 (s, 1H), 7.75 (s, 1H), 7.58 (d, J=8.6 Hz, 1H), 7.01 and 6.96 (dd, J=2.0 and 8.6 Hz, 1H), 1.59 (s, 9H); MS(ES) m/z 219 (M+).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined extracts were washed with brine (10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a residue which
  5. customwas purified by chromatography (silica, 10% to 20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-21cc3423f8b445c3b886121bfccb8912
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956036B1

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