Potassium Phosphate, Tribasic → HCID 70945481, Verbindung

HRID 517998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517998
[CH3:1][N:2]([CH2:10][CH2:11][O:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][N:14]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[NH2:32][C:33]1[C:34]([C:42]#[N:43])=[N:35][C:36](Cl)=[CH:37][C:38]=1[NH:39][CH3:40].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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]>[NH2:32][C:33]1[C:38]([NH:39][CH3:40])=[CH:37][C:36]([C:16]2[CH:15]=[N:14][C:13]([O:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[C:18]([C:19]([F:20])([F:21])[F:22])[CH:17]=2)=[N:35][C:34]=1[C:42]#[N:43]

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrileHCID 69932325HCID 69932325, Verbindung

Produkt 1

HCID 70945481HCID 70945481, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of tert-butyl methyl(2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-yloxy)ethyl)carbamate (440 mg), 3-amino-6-chloro-4-(methylamino)picolinonitrile (135 mg), tris(dibenzylideneacetone)dipalladium (0) (34.9 mg), tricyclohexylphosphine (25.7 mg) and potassium phosphate (327 mg) in 1,4-dioxane (10 ml) and water (5 ml) was stirred at 100° C. for 2 h. The reaction mixture was cooled and partitioned between water and ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated. Purified by Biotage SNAP cartridge KP-Sil column (25 g, heptane:ethyl acetate=1:0, 3:1, 2:1, 1:1 to 1:2) to give 170 mg orange amorphous as tert-butyl 2-(5-amino-6-cyano-4-(methylamino)-5′-(trifluoromethyl)-2,3′-bipyridin-6′-yloxy)ethyl(methyl)carbamate (49%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between water and ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified by Biotage SNAP cartridge KP-Sil column (25 g, heptane:ethyl acetate=1:0, 3:1, 2:1, 1:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-17b238368e8745368278ae3dc4d6fdcb
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115126B2

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