3-(Methylcarbamoyl)benzeneboronic acid → HCID 59593137, Verbindung

HRID 2098819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098819
Cl[C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9](I)=[C:8]([CH3:12])[C:6]=2[N:7]=1.[CH3:19][NH:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].CC1(C)C(C)(C)OB([C:40]2[CH:48]=[CH:47][CH:46]=[C:45]3[C:41]=2[CH:42]=[N:43][NH:44]3)O1>C([O-])([O-])=O.[Na+].[Na+].C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:44]1[C:45]2[C:41](=[C:40]([C:2]3[N:3]=[C:4]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[C:5]4[S:10][C:9]([C:27]5[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=5)[C:21]([NH:20][CH3:19])=[O:22])=[C:8]([CH3:12])[C:6]=4[N:7]=3)[CH:48]=[CH:47][CH:46]=2)[CH:42]=[N:43]1

Komponenten

7

Edukt 3

HCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 595928802-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine

Produkt 1

HCID 59593137HCID 59593137, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysator2×HCID 6342AcetonitrileLösungsmittel2×HCID 10340Sodium CarbonateLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

2-Chloro-6-iodo-7-methyl-4-morpholinothieno[3,2-d]pyrimidine from Example 12 (0.1 g, 0.3 mmol), 3-(N-Methylaminocarbonyl)benzeneboronic acid (50 mg, 0.3 mmol), and bis(triphenylphosphine)palladium(II) dichloride (9 mg, 13 μmol) in 1 M aqueous Na2CO3 (0.5 mL) and acetonitrile (0.5 mL) were heated to 100° C. in a sealed microwave reactor for 10 min. Upon completion, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 (122 mg, 0.5 mmol), bis(triphenylphosphine)palladium(II) dichloride (9 mg, 13 mmol), 1 M aqueous Na2CO3 (1 mL), and acetonitrile (1 mL) were added into the same pot. The reaction mixture was heated to 150° C. in a sealed microwave reactor for 20 min. The mixture was extracted with EtOAc and CF2Cl2. The combined organics were concentrated to yield 358 after reverse phase HPLC purification (2 mg). MS (Q1) 485 (M)+

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc and CF2Cl2
  2. concentrationThe combined organics were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d7cba1502d4544299974e1ee17b82613
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450315B2

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