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Potassium Phosphate, Tribasic → N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide

HRID 593694
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 593694
Cl[C:2]1[C:11]2[C:6](=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:18])=[N:4][N:3]=1.[C:19]([NH:23][S:24]([C:27]1[CH:28]=[N:29][CH:30]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:32]=1)(=[O:26])=[O:25])([CH3:22])([CH3:21])[CH3:20].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C([O-])=O.[NH4+].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[C:19]([NH:23][S:24]([C:27]1[CH:28]=[N:29][CH:30]=[C:31]([C:2]2[C:11]3[C:6](=[C:7]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:8]=[CH:9][CH:10]=3)[C:5]([Cl:18])=[N:4][N:3]=2)[CH:32]=1)(=[O:26])=[O:25])([CH3:22])([CH3:20])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 90386425N-(tert-Butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamideHCID 904244121,4-Dichloro-5-phenylphthalazine

Produkt 1

HCID 90424399N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamideAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 75806
Tricyclohexylphosphine
Katalysator
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel
HCID 2723923Ammonium formateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a solution of 1,4-dichloro-5-phenylphthalazine (0.400 g, 1.45 mmol) and N-(tert-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-sulfonamide (0.742 g, 2.18 mmol) (Johnson et al., WO 2011/28741) in 1,4-dioxane (15 mL) and water (3 mL) was added K3PO4 (0.617 g, 2.91 mmol) and the contents purged with nitrogen for 10 min. Tricyclohexylphosphine (10.2 mg, 0.0360 mmol) was added followed by Pd2(dba)3 (0.0130 g, 0.0150 mmol) and heated at 95° C. for 12 h. The reaction mixture was allowed to cool to ambient temperature. The reaction mixture was diluted with HCOONH4 buffer (pH˜5) solution and extracted with EtOAc (3×75 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by combiflash (REDISEP®, silica gel, 12 g, 30% EtOAc/hexanes) to obtain N-(tert-butyl)-5-(4-chloro-5-phenylphthalazin-1-yl)pyridine-3-sulfonamide (0.500 g, 76.0%) as a pale yellow solid. LCMS (Condition 11): retention time 1.04 min, [M+1]=453.2. 1H NMR (400 MHz, DMSO-d6) δ 1.20 (s, 9 H), 7.43-7.46 (m, 2 H), 7.50-7.54 (m, 3 H), 7.98 (s, 1 H), 7.99 (dd, J=1.2 Hz, J=8.0 Hz, 1H), 8.03 (dd, J=1.2 Hz, J=7.2 Hz, 1 H), 8.15 (dd, J=7.2 Hz, J=8.0 Hz, 1 H), 8.58 (t, J=2.0 Hz, 1 H), 9.17 (d, J=2.0 Hz, 1 H), 9.23 (d, J=2.0 Hz, 1 H).

Aufarbeitung

  1. customthe contents purged with nitrogen for 10 min
  2. temperatureto cool to ambient temperature
  3. extractionextracted with EtOAc (3×75 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by combiflash (REDISEP®, silica gel, 12 g, 30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8fe2ec71ce164915917a24db71f61151
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242966B2

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