Potassium Phosphate, Tribasic → 4-(3-Cyclopropyl-indole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide

HRID 1178977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178977
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20](I)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:31]1([C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]([S:15]([C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][C:5]4[CH:29]=[CH:30][C:2]([F:1])=[CH:3][CH:4]=4)=[O:28])=[CH:10][CH:11]=3)(=[O:17])=[O:16])[CH:19]=2)[CH2:33][CH2:32]1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 58975061N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide

Produkt 1

HCID 589750114-(3-Cyclopropyl-indole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Combine N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide (0.50 g, 0.94 mmol), cyclopropylboronic acid (0.24 g, 2.8 mmol), tricyclohexylphosphine (0.05 g, 0.18 mmol), potassium phosphate (0.70 g, 3.30 mmol), and palladium acetate (0.02 g, 0.09 mmol) in a mixture of toluene (15 mL) and water (0.4 mL). Heat to 100° C. under nitrogen for 18 hours, filter through celite, and wash solids with EtOAc. Wash EtOAc with saturated NaHCO3 (30 mL), then dry with Na2SO4, and concentrate under vacuum. Purify by flash column on silica gel eluting with 0-50% EtOAc in hexanes to give the title compound (0.25 g, 60%). MS (ES) 449.2 (M+1)+, 447.4 (M−1)−.

Aufarbeitung

  1. filtrationfilter through celite
  2. washwash solids with EtOAc
  3. dry with materialWash EtOAc with saturated NaHCO3 (30 mL), then dry with Na2SO4
  4. concentrationconcentrate under vacuum
  5. customPurify by flash column on silica gel eluting with 0-50% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f07dbabf5c5547138b6ced4349f08f3a
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276516B2

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