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Sodium Carbonate → (4-{4-[6-(2-Methyl-6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

HRID 76046
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 76046
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[C:10]([CH3:19])=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1.[CH3:20][O:21][C:22](=[O:45])[CH2:23][CH:24]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][CH:31]=2)[CH2:26][CH2:25]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:20][O:21][C:22](=[O:45])[CH2:23][CH:24]1[CH2:25][CH2:26][CH:27]([C:30]2[CH:31]=[CH:32][C:33]([C:2]3[CH:7]=[N:6][C:5]([NH:8][C:9]4[C:10]([CH3:19])=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=4)=[CH:4][CH:3]=3)=[CH:34][CH:35]=2)[CH2:28][CH2:29]1
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Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 57992171Methyl 2-(trans-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclohexyl)acetateHCID 66615910(5-Bromo-pyridin-2-yl)-(2-methyl-6-trifluoromethyl-pyridin-3-yl)-amine

Produkt 1

HCID 66615758(4-{4-[6-(2-Methyl-6-trifluoromethyl-pyridin-3-ylamino)-pyridin-3-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(5-Bromo-pyridin-2-yl)-(2-methyl-6-trifluoromethyl-pyridin-3-yl)-amine (290 mg, 0.87 mmol) and {4-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (312 mg, 0.87 mmol) were dissolved in anhydrous DME (3 mL) in a pressure vessel. PdCl2dppf (21 mg, 0.026 mmol) was added, followed by aqueous sodium carbonate (2M, 0.870 mL, 1.74 mmol). The mixture was sparged with nitrogen for 10 minutes, then the vessel was sealed and heated at 80° C. for 18 hours. The mixture was partitioned between EtOAc and water, washed with brine, dried with magnesium sulfate, filtered, and concentrated via rotary evaporation. The crude material was purified via column chromatography on silica gel, eluting with a gradient of EtOAc/hexanes (7-50%) to obtain the target compound as a solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08-1.21 (m, 2H) 1.50 (td, J=12.44, 10.23 Hz, 2H) 1.81 (m, 4H) 2.25 (d, J=6.57 Hz, 2H) 2.59 (s, 3H) 3.60 (s, 3H) 7.22 (d, J=8.59 Hz, 1H) 7.31 (d, J=8.34 Hz, 2H) 7.57 (d, J=8.34 Hz, 2H) 7.66 (d, J=8.59 Hz, 1H) 7.97 (dd, J=8.59, 2.53 Hz, 1H) 8.48 (d, J=2.53 Hz, 1H) 8.64 (s, 1H) 8.66 (d, J=8.34 Hz, 1H); MS-(M+H)+484.3.

Aufarbeitung

  1. customThe mixture was sparged with nitrogen for 10 minutes
  2. customthe vessel was sealed
  3. customThe mixture was partitioned between EtOAc and water
  4. washwashed with brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated via rotary evaporation
  8. customThe crude material was purified via column chromatography on silica gel
  9. washeluting with a gradient of EtOAc/hexanes (7-50%)

Quellen und Nachweise

ORD-Eintrag
ord-9b90d06bdb0242048145e648c9543ed3
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835451B2

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