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1,2-Dimethoxyethane → Methyl 3-(2-hydroxypropan-2-yl)-1-(thiophen-3-yl)-1H-indazole-6-carboxylate

HRID 1047638
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1047638
[CH2:1]=[C:2]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[N:6]([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[N:5]=1)[CH3:3].[BH4-].C([N+](CC)(CC)CC)C.C(COC)[O:33]C>CO.C1C=CC(C2C3=NC(C=C3)=C(C3C=CC=CC=3)C3[N-]C(=CC=3)C(C3C=CC=CC=3)=C3C=CC(=N3)C(C3C=CC=CC=3)=C3[N-]C=2C=C3)=CC=1.[Co+2]>[OH:33][C:2]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[N:6]([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[N:5]=1)([CH3:3])[CH3:1]
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Komponenten

6

Edukt 3

HCID 80711,2-DimethoxyethaneHCID 28251Tetraethylammonium tetrahydroborateHCID 66661623Methyl 3-(prop-1-en-2-yl)-1-(thiophen-3-yl)-1H-indazole-6-carboxylate

Produkt 1

HCID 66661520Methyl 3-(2-hydroxypropan-2-yl)-1-(thiophen-3-yl)-1H-indazole-6-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 518893
meso-Tetraphenylporphine-Co(II)
Katalysator
HCID 887MethanolLösungsmittel

Versuchsvorschrift

Methyl 3-(prop-1-en-2-yl)-1-(thiophen-3-yl)-1H-indazole-6-carboxylate (1.0763 g, 3.61 mmol) was dissolved in dimethoxyethane (90 ml)/MeOH (90 ml) at 25° C. Cobalt(II) meso-tetraphenylporphine (25.6 mg, 0.038 mmol) and tetraethylammonium borohydride (1.316 g, 9.07 mmol) were added sequentially. The reaction mixture was allowed to stir for 1.25 h. The reaction was stopped, quenched by addition of saturated aqueous ammonium chloride (100 mL), and the mixture extracted with ethyl acetate (3×80 mL). The combined organic phases were washed with saturated aqueous sodium chloride (1×80 mL), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography (RediSep SiO2, 330 g column) on a CombiFlash Rf purification system eluting with ethyl acetate-hexanes (0-45%). The title compound (912.2 mg, 2.88 mmol, 80% yield) was recovered as an orange solid. LC-MS: [M+1]=317.1.

Aufarbeitung

  1. customquenched by addition of saturated aqueous ammonium chloride (100 mL)
  2. extractionthe mixture extracted with ethyl acetate (3×80 mL)
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride (1×80 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash chromatography (RediSep SiO2, 330 g column) on a CombiFlash Rf purification system
  8. washeluting with ethyl acetate-hexanes (0-45%)

Quellen und Nachweise

ORD-Eintrag
ord-18cb3265a838422c81948ecfad00141c
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08569512B2

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