2-[3-(2-Methoxyethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 68465011, Verbindung

HRID 506201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506201
I[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:9]=1[NH:10][C:11]1[C:12]([CH3:20])=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:7]#[N:8].[CH3:21][O:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:29]=[CH:30][CH:31]=1>COCCOC.C([O-])(O)=O.[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][O:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[C:30]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([C:9]=2[NH:10][C:11]2[C:12]([CH3:20])=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[C:7]#[N:8])[CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 2

HCID 595587402-[3-(2-Methoxyethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 684438315-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile

Produkt 1

HCID 68465011HCID 68465011, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 5-iodo-4[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile (100 mg, 0.27 mmol), 2-[3-(2-methoxyethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (98 mg, 0.35 mmol) and tetrakis(triphenylphosphine)palladium(0) (16 mg, 0.014 mmol) in DME (6 mL) and saturated aqueous NaHCO3 (4 mL) was heated at 95° C. for 2 h, cooled to room temperature and partitioned between dichloromethane and water. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo, and the residue was purified by flash column chromatography (MeOH/CH2Cl2, 1% to 5%) to provide 71 mg (66%) of 5-[3-(2-methoxyethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile as a tan solid. HPLC retention time: 8.3 min.(g); MS: 399.3 (M+H); melting range: 158-160° C.; and HRMS: 399.18291.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash column chromatography (MeOH/CH2Cl2, 1% to 5%)

Quellen und Nachweise

ORD-Eintrag
ord-b2c8ac49a46340b786b41390b92fa431
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781591B2

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