Sodium Carbonate → 2-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amine

HRID 1698073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698073
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][O:13][C:14]1[N:15]=[CH:16][C:17]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 529878072-Bromobenzo[d]thiazol-6-amine

Produkt 1

HCID 248035652-(6-Methoxypyridin-3-yl)-1,3-benzothiazol-6-amineAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 2-bromo-1,3-benzothiazol-6-amine (53 mg, 0.23 mmol), 2-methoxy-5-pyridineboronic acid (50 mg, 0.327 mmol), Pd(dppf)Cl2*DCM (8 mg, 0.01 mmol) and sodium carbonate (0.1 g, 1 mmol) in THF/water (9:1, 3 mL) was heated at 140° C. for 10 minutes in a microwave reactor under argon atmosphere. The mixture was filtered and washed with THF/water (9:1). After having added DCM to the filtrate, the organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash column chromatography (20 to 70% ethyl acetate in heptane), to yield the title compound (57 mg) as an off-white solid. 1H NMR (CHLOROFORM-d) δ 8.68 (d, 1H) 8.16 (dd, 1H) 7.74 (d, 1H) 7.06 (d, 1H) 6.70-6.81 (m, 2H) 3.94 (s, 3H) 3.77 (s, 2H); MS m/z (M+H) 258.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washwashed with THF/water (9:1)
  3. additionAfter having added DCM to the filtrate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (20 to 70% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-659e8d2bd817477f9fb1ccc4913eba1b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163928B2

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