Potassium Phosphate, Tribasic → Methyl [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetate

HRID 474144

Reaktionsgleichung

Reaktionsgleichung von HRID 474144
Cl[C:2]1[C:3]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:19]1([C:2]2[C:3]([C:8]3[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH2:21][CH2:20]1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 59535943Methyl 2-(4-(3-chloropyrazin-2-yl)phenyl)acetate

Produkt 1

HCID 59535940Methyl [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetateAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 0.15 g (0.57 mmol) of methyl [4-(3-chloropyrazin-2-yl)phenyl]acetate acid in 3.0 mL of toluene and 0.15 mL of water were added 63.8 mg (0.74 mmol) of cyclopropyl boronic acid, 16 mg (0.06 mmol) of tricyclohexylphosphine, 7.8 mg (0.009 mmol) of Pd2(dba)3, and 0.42 g (2.0 mmol) of potassium phosphate. The resulting suspension was degassed for 10 minutes. After 1 h in the microwave at 140° C., the reaction mixture was cooled, diluted with CH2Cl2, wash three times with water, and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc in hexanes) afforded 0.10 g (65%) methyl [4-(3-cyclopropylpyrazin-2-yl)phenyl]acetate. 1H NMR (CDCl3, 400 MHz) δ 8.35 (m, 2H); 7.68 (d, J=8.06 Hz, 2H); 7.41 (d, J=8.06 Hz, 2H); 3.72 (s, 3H); 3.71 (s, 2H); 2.22 (m, 1H); 1.19 (m, 2H); 0.99 (m, 2H). ES-MS M+1=269.1.

Aufarbeitung

  1. customThe resulting suspension was degassed for 10 minutes
  2. temperaturethe reaction mixture was cooled
  3. additiondiluted with CH2Cl2
  4. washwash three times with water
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography (silica gel, linear gradient 0-40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6249aada39304de5ad02af7adb819570
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637513B2

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