Potassium Carbonate → Tert-butyl[5-(6-carbamoyl-1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamate

HRID 1698106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698106
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([NH2:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:14]([O:18][C:19](=[O:36])[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25](B2OCC(C)(C)CO2)=[CH:24][N:23]=1)([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.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]>[C:14]([O:18][C:19](=[O:36])[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([C:11](=[O:12])[NH2:13])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:24][N:23]=1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 575534032-Chloro-1,3-benzothiazole-6-carboxamideHCID 86626541tert-Butyl [5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate

Produkt 1

HCID 86626543Tert-butyl[5-(6-carbamoyl-1,3-benzothiazol-2-yl)pyridin-2-yl]methylcarbamateAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-chloro-1,3-benzothiazole-6-carboxamide (77 mg, 0.36 mmol), tert-butyl[5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)pyridin-2-yl]methylcarbamate (0.174 g, 0.54 mmol), Pd(dppf)Cl2*DCM (30 mg, 0.036 mmol) and 2 M aq. K2CO3 (0.8 mL) in DMF (2 mL) was stirred under argon at 80° C. for 2 h. The reaction mixture was filtered and the filtrate was partitioned between EtOAc and H2O. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (Heptane/EtOAc gradient) gave the product (66 mg) as a white solid. MS m/z (M−H) 383.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was partitioned between EtOAc and H2O
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-94b465f84f4d4f65a2afb4115f57a524
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163928B2

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