Potassium Phosphate, Tribasic → HCID 68328328, Verbindung

HRID 634210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 634210
[CH:1]([NH:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH:14]=[C:13]3B2OC(C)(C)C(C)(C)O2)=[N:8][N:9]=1)([CH3:3])[CH3:2].Cl[C:39]1[CH:44]=[N:43][CH:42]=[C:41]([CH:45]2[CH2:47][CH2:46]2)[N:40]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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]>[CH:45]1([C:41]2[N:40]=[C:39]([C:13]3[C:12]4[C:16](=[CH:17][CH:18]=[C:10]([C:7]5[O:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:9][N:8]=5)[CH:11]=4)[N:15]([S:19]([C:22]4[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=4)(=[O:20])=[O:21])[CH:14]=3)[CH:44]=[N:43][CH:42]=2)[CH2:47][CH2:46]1

Komponenten

6

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 649849712-Chloro-6-cyclopropylpyrazineHCID 68328163HCID 68328163, Verbindung

Produkt 1

HCID 68328328HCID 68328328, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a 20 mL microwave vial was added N-isopropyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (167 mg, 0.379 mmol), 2-chloro-6-cyclopropylpyrazine (CombiPhos Catalyst Inc., 64.5 mg, 0.42 mmoles), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (10.9 mg, 0.023 mmol), Pd2(dba)3 (10.4 mg, 0.011 mmol), and K3PO4 (242 mg, 1.138 mmol) followed by purging with argon. The solids were treated with dioxane (4.0 mL) and H2O (0.4 mL) and heated in the microwave at 120° C. for 20 min. The mixture was treated with H2O and extracted with EtOAc, dried over MgSO4, filtered and concentrated. Purification with flash chromatography (eluting with 5-100% EtOAc in Hex) afforded 5-(3-(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (104.4 mg, 54%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 515.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.87 (1H, s), 8.74 (1H, s), 8.42 (1H, s), 8.16 (1H, s), 8.07-8.11 (1H, m), 7.98-8.03 (1H, m), 7.84 (2H, d, J=8.4 Hz), 7.28 (2H, s), 3.97-4.08 (1H, m), 2.36 (3H, s), 2.14 (1H, td, J=8.5, 4.2 Hz), 1.35 (6H, d, J=6.5 Hz), 1.24-1.30 (2H, m), 1.10-1.17 (2H, m).

Aufarbeitung

  1. customby purging with argon
  2. additionThe solids were treated with dioxane (4.0 mL) and H2O (0.4 mL)
  3. additionThe mixture was treated with H2O
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washwith flash chromatography (eluting with 5-100% EtOAc in Hex)

Quellen und Nachweise

ORD-Eintrag
ord-4a74a56750184f49a6f29e478d2961e8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321756B2

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