Sodium Bicarbonate → 2-(4-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-cyclopentanecarboxylic acid methyl ester

HRID 1691951

Reaktionsgleichung

Reaktionsgleichung von HRID 1691951
Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12]=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:14][C:15]=2[C:16]([F:19])([F:18])[F:17])=[O:10])=[CH:4][CH:3]=1.C1(C2OC(C(F)(F)F)=C(C(O)=O)N=2)C=CC=CC=1.BrC1N=CC(N)=CC=1.[CH3:52][O:53][C:54]([CH:56]1[CH2:60][CH2:59][CH2:58][CH:57]1[C:61](=[O:77])[C:62]1[CH:67]=[CH:66][C:65](B2OC(C)(C)C(C)(C)O2)=[CH:64][CH:63]=1)=[O:55].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:52][O:53][C:54]([CH:56]1[CH2:60][CH2:59][CH2:58][CH:57]1[C:61](=[O:77])[C:62]1[CH:63]=[CH:64][C:65]([C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]3[N:12]=[C:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:14][C:15]=3[C:16]([F:18])([F:19])[F:17])=[O:10])=[CH:6][N:7]=2)=[CH:66][CH:67]=1)=[O:55]

Komponenten

9

Edukt 5

HCID 516892Sodium BicarbonateHCID 6428116-Bromopyridin-3-amineHCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 219858742-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoyl]-cyclopentanecarboxylic acid methyl esterHCID 576521452-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-bromo-pyridin-3-yl)-amide

Produkt 1

HCID 251221862-(4-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-cyclopentanecarboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

2-(4-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-cyclopentanecarboxylic acid methyl ester was prepared through a standard Suzuki coupling procedure by mixing 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-bromo-pyridin-3-yl)-amide (prepared using a similar coupling procedure as described above from 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid and 6-bromo-pyridin-3-ylamine), 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoyl]-cyclopentanecarboxylic acid methyl ester, palladium tetrakis(triphenylphosphine) and aqueous sodium bicarbonate solution in toluene and ethanol, and heating this mixture to 160° C. under microwave condition for 20 min. Aqueous workup followed by silica gel chromatography separation gave 2-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-cyclopentanecarboxylic acid methyl ester as light yellow solid. LCMS calcd for C30H24F3N3O5 (m/e) 563, obsd 564 (M+H).

Aufarbeitung

  1. custom2-(4-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-cyclopentanecarboxylic acid methyl ester was prepared through a standard Suzuki coupling procedure
  2. customprepared
  3. customAqueous workup followed by silica gel chromatography separation

Quellen und Nachweise

ORD-Eintrag
ord-630040547ecb4903acf40a66f97305a6
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153644B2

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