Potassium Phosphate, Tribasic → HCID 53373964, Verbindung

HRID 335818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 335818
Cl[C:2]1[N:7]=[CH:6][C:5]2[O:8][C:9]3[C:14]([C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]=2[CH:3]=1)=[CH:13][C:12](B1OC(C)(C)C(C)(C)O1)=[CH:11][CH:10]=3.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:38][C:39]1[C:44](I)=[C:43]([F:46])[CH:42]=[CH:41][N:40]=1>O1CCOCC1.O.CCOC(C)=O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[F:38][C:39]1[C:44]([C:12]2[CH:13]=[C:14]3[C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]4[CH:3]=[C:2]([C:15]5[CH2:14][CH2:9][O:8][CH2:5][CH:4]=5)[N:7]=[CH:6][C:5]=4[O:8][C:9]3=[CH:10][CH:11]=2)=[C:43]([F:46])[CH:42]=[CH:41][N:40]=1

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 121758042,4-DIFLUORO-3-IODOPYRIDINEHCID 86658464HCID 86658464, Verbindung

Produkt 1

HCID 53373964HCID 53373964, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)KatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 20 mL glass microwave reaction vessel was charged with (S)-3-chloro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.251 g, 0.608 mmol), potassium phosphate (0.269 g, 1.266 mmol), 2,4-difluoro-3-iodopyridine (0.122 g, 0.506 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (0.036 g, 0.051 mmol) in dioxane (3.2 mL) and water (0.8 mL). The reaction mixture was heated at 100° C. for 30 min in microwave reactor. After cooling the rt the mixture was diluted with EtOAc and water. The aqueous layer was washed twice with saturated Na2CO3. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by silica gel chromatography (2-10% MeOH—CH2Cl2) to provide the desired product as a brown residue.

Aufarbeitung

  1. temperatureAfter cooling the rt the mixture
  2. washThe aqueous layer was washed twice with saturated Na2CO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by silica gel chromatography (2-10% MeOH—CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-41255c7fc8d446d6a8c584bccf1d945d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883782B2

Notizen zur Reaktion

Wird geladen…