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Sodium Carbonate → 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butylpyridine-3-sulfonamide

HRID 384744
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 384744
Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])[CH:5]=[N:6][CH:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:40]1[CH:41]=[CH:42][C:43]2[N:44]([N:46]=[C:47]([NH2:49])[N:48]=2)[CH:45]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CCO.O1CCOCC1>[C:12]([NH:11][S:8]([C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:40]2[CH:41]=[CH:42][C:43]3[N:44]([N:46]=[C:47]([NH2:49])[N:48]=3)[CH:45]=2)[CH:3]=1)(=[O:10])=[O:9])([CH3:15])([CH3:14])[CH3:13]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 252159406-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amineHCID 617949515-Bromo-N-tert-butylpyridine-3-sulfonamide

Produkt 1

HCID 42623223
5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butylpyridine-3-sulfonamide
Ausbeute 184,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

5-bromo-N-tert-butylpyridine-3-sulfonamide (375 mg, 0.986 mmol), bis(pinacolato) diboron (276 mg, 1.085 mmol), potassium acetate (290 mg, 2.96 mmol), [1,1′bis(diphenylphosphino)ferrocene]dichloro-palladium (II) complex with CH2Cl2 (40 mg, 0.049 mmol) and dioxane (3 ml) were heated to 120° C. for 60 minutes in the microwave. After this time aryl bromide (A) (147 mg, 0.69 mmol), Na2CO3 (2M aqueous solution, 2 mL), EtOH (0.4 ml) and a further portion of [1,1′bis(diphenylphosphino)ferrocene]dichloro-palladium (II) complex with CH2Cl2 was added and reaction mixture heated further for 60 minutes at 120° C. in the microwave. After this time the solvents were removed in vacuo and the brown residue redissolved in 2M HCl (30 mL), the aqueous phase was washed with ethyl acetate (3×20 mL) and then neutralized with concentrated NaOH to pH 7.0. The aqueous phase was then extracted with ethyl acetate (3×20 mL), the organic extracts were combined, dried over sodium sulfate, filtered and the solvent removed in vacuo to afford the desired product as a brown solid (441 mg, 54%).

Aufarbeitung

  1. customreaction mixture
  2. customAfter this time the solvents were removed in vacuo
  3. dissolutionthe brown residue redissolved in 2M HCl (30 mL)
  4. washthe aqueous phase was washed with ethyl acetate (3×20 mL)
  5. extractionThe aqueous phase was then extracted with ethyl acetate (3×20 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9d0d2cf4a8984810b5cc3dab931eaac6
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367830B2

Notizen zur Reaktion

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