Methanol → 4-(4-Phenylamino-[1,3,5]triazin-2-yl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 2217182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217182
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:21])=[O:20])[CH:7]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:9]=1)=[O:4].Cl[C:32]1[N:37]=[CH:36][N:35]=[C:34]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:33]=1.C(=O)([O-])[O-].[Na+].[Na+].CO>C(OCC)(=O)C.C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:19]([C:22]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=2[CH3:30])(=[O:20])=[O:21])[CH:7]=[C:8]([C:36]2[N:35]=[C:34]([NH:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:33]=[CH:32][N:37]=2)[CH:9]=1)=[O:4]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 199377234-chloro-N-phenyl-1,3,5-triazin-2-amineHCID 59767810Methyl 1-(mesitylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 597678114-(4-Phenylamino-[1,3,5]triazin-2-yl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl esterAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a 10 mL flask was added 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (1.0 equivalent, 0.34 mmol, 149 mg), (4-chloro-[1,3,5]triazin-2-yl)-phenyl-amine (1.1 equivalent, 0.37 mmol, 78 mg), tetrakistriphenylphosphine palladium (0.2 equivalent, 0.07 mmol, 80 mg), sodium carbonate (1 mL, 2 N), methanol (1 mL) and benzene (5 mL). The resulting mixture was heated at 80° C. for 2 hours then diluted in ethyl acetate and washed with water, brine. The organic layer was dried over sodium sulfate then concentrated under vacuum. The crude mixture was then purified by prep HPLC to afford 55 mg of the title compound. HPLC, Rt=8.8 min, FIA, ES+=478.1.

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationthen concentrated under vacuum
  4. customThe crude mixture was then purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-693e2d5d9747448bbd0429d061475fe0
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407962B2

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