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2-Isopropoxy-6-(tributylstannyl)pyridine → tert-butyl (3-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-thiadiazol-5-yl)carbamate

HRID 634263
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 634263
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[S:13][N:12]=3)[CH:9]=2)[N:4]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:3]=1.[CH:34]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([Sn](CCCC)(CCCC)CCCC)[N:39]=1)([CH3:36])[CH3:35]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:34]([O:37][C:38]1[N:39]=[C:40]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[S:13][N:12]=4)[CH:9]=3)[N:4]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:25])=[O:26])[CH:3]=2)[CH:41]=[CH:42][CH:43]=1)([CH3:36])[CH3:35]
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Komponenten

6

Edukt 2

HCID 683286192-Isopropoxy-6-(tributylstannyl)pyridineHCID 86725113tert-butyl 3-(3-iodo-1-tosyl-1H-indol-5-yl)-1,2,4-thiadiazol-5-ylcarbamate

Produkt 1

HCID 86725114tert-butyl (3-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-thiadiazol-5-yl)carbamateAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of tert-butyl (3-(3-iodo-1-tosyl-1H-indol-5-yl)-1,2,4-thiadiazol-5-yl)carbamate (0.6 g, 1.0 mmol) and 2-isopropoxy-6-(tributylstannyl)pyridine (0.429 g, 1.0 mmol) in DMF (10 mL) was bubbled N2 gas for 15 min. To the above mixture, CuI (95 mg, 0.5 mmol.) and Pd(PPh3)4 (12 mg, 0.1 mmol) were added and N2 gas was bubbled for another 15 min. The reaction was heated at 90° C. for 1 h. The reaction mixture was quenched with H2O (10 mL) and extracted with CHCl3 (2×25 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified by neutral alumina column chromatography (eluent: 20% EtOAc in petroleum ether) to give tert-butyl (3-(3-(6-isopropoxypyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-thiadiazol-5-yl)carbamate (0.35 g, 57.4%). MS (ESI, pos. ion) m/z: 606.4 (M+1); 1H NMR (DMSO-d6, 400 MHz): δ 9.33 (s, 1H), 8.52 (s, 1H), 8.16-8.08 (m, 2H), 7.97 (d, J=8 Hz, 2H), 7.76 (t, J=7.6 Hz, 1H), 7.63 (d, J=7.6 Hz, 2H), 7.40 (d, J=8.4 Hz, 1H), 6.69 (d, J=8 Hz, 1H), 5.52-5.49 (m, 1H), 2.30 (s, 3H), 1.40 (d, J=6 Hz, 6H).

Aufarbeitung

  1. customwas bubbled N2 gas for 15 min
  2. customN2 gas was bubbled for another 15 min
  3. customThe reaction mixture was quenched with H2O (10 mL)
  4. extractionextracted with CHCl3 (2×25 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by neutral alumina column chromatography (eluent: 20% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-cb175bdc7ea941ba9d2006a7b65178e6
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321756B2

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