Potassium Carbonate → Ethyl 3'-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-4-carboxylate

HRID 530392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530392
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]([NH:27][C:28]3[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=3)[CH:24]=[CH:25][CH:26]=2)O1.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.CN(C=O)C>[F:37][C:34]([F:35])([F:36])[C:32]1[CH:31]=[CH:30][N:29]=[C:28]([NH:27][C:23]2[CH:22]=[C:21]([C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=3)[CH:26]=[CH:25][CH:24]=2)[N:33]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 22043Ethyl 4-bromobenzoateHCID 58456307N-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Produkt 1

HCID 90041226Ethyl 3'-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Ethyl 4-bromobenzoate (73.2 mg, 0.301 mmol) was added to a mixture of N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (100 mg, 0.274 mmol), PdCl2(dppf)-CH2Cl2 adduct (22.4 mg, 0.027 mmol), DMF (5.5 mL), and aqueous K2CO3 (2 M, 0.411 mL, 0.822 mmol) and the reaction mixture was evacuated and back flushed with Argon. The reaction mixture was heated in the microwave reactor for 2 hours at 85° C. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) to afford ethyl 3′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-4-carboxylate as an off-white solid. MS ESI calc'd. for C20H17F3N3O2[M+H]+ 388, found 388. 1H NMR (500 MHz, CDCl3): δ 8.67 (d, J=4.9 Hz, 1H); 7.96 (s, 1H); 7.61 (t, J=6.2 Hz, 3H); 7.55 (s, 1H); 7.47-7.40 (m, 1H); 7.40 (d, J=7.9 Hz, 2H); 7.35 (d, J=7.7 Hz, 1H); 7.06 (d, J=4.9 Hz, 1H); 4.22 (q, J=7.1 Hz, 2H); 1.31 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. customthe reaction mixture was evacuated
  2. customback flushed with Argon
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-37c51c0918a34f29830c867fac9c1df1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353066B2

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