Iodine → HCID 178451735, Verbindung

HRID 1520017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520017
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[CH:9][CH:10]=2)[CH:5]=[N:4]1.[I:25]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[I:25][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[CH:7]=2)[NH:3][N:4]=1

Komponenten

6

Edukt 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 49760224tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylate

Produkt 1

HCID 178451735HCID 178451735, VerbindungAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

KOH (141.5 mg; 2.52 mmol; 3.8 eq.) pellets were added in small portion during 10 min to a solution of tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylate (200 mg; 0.66 mmol; 1.0 eq.) and iodine (0.34 g; 1.33 mmol; 2.0 eq.) in dry DMF (6 mL). The reaction mixture was stirred O/N at RT. It was then poured into a saturated solution of Na2S2O3 (100 mL) and extracted three times with ether. Combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow foam (225 mg, 79%). 1H NMR (300 MHz, DMSO-d6) δ 13.41 (brs, 1H), 7.48 (d, J=8.6 Hz, 1H), 7.35 (dd, J=8.7, 1.3 Hz, 1H), 7.20 (s, 1H), 4.26-3.94 (m, 2H), 2.93-2.74 (m, 3H), 1.99-1.70 (m, 2H), 1.67-1.47 (m, 2H), 1.42 (s, 9H). HPLC (Condition A): Rt 5.10 min (purity 100%).

Aufarbeitung

  1. extractionextracted three times with ether
  2. washCombined organic layers were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-004b6a6db89b4b27be84bae12c2b62d1
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073892B2

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