Trifluoromethanesulfonic anhydride → Methyl 3-(3'-methylaminobiphenyl-4-yl)propanoate

HRID 250827

Reaktionsgleichung

Reaktionsgleichung von HRID 250827
O[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.C(=O)([O-])O.[Na+].[CH3:34][NH:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1>ClCCl.C(N(CC)CC)C.CN(C)C=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:34][NH:35][C:36]1[CH:41]=[C:40]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=2)[CH:39]=[CH:38][CH:37]=1

Komponenten

11

Edukt 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 516892Sodium BicarbonateHCID 23558980[3-(Methylamino)phenyl]boronic acid

Produkt 1

HCID 67273433Methyl 3-(3'-methylaminobiphenyl-4-yl)propanoateAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 62657Potassium Phosphate, TribasicLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.0 g (5.5 mmol, 1.0 eq) of methyl 3-(4-hydroxyphenyl)propanoate is dissolved in 8 mL of dichloromethane in the presence of 1 ml of triethylamine. 1.12 mL (6.6 mmol, 1.2 eq) of triflic anhydride are added at 0° C. The reaction mixture is stirred for 1 hour at 0° C. The reaction is stopped by addition of 50 mL of saturated sodium hydrogen carbonate solution and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then filtered on silica gel (1/1 heptane/ethyl acetate). After evaporating off the solvents, the oil obtained is dissolved in 6 mL of an 8/2 mixture of dimethylformamide and of 2M potassium phosphate solution. 1.0 g (6.6 mmol, 1.2 eq) of N-methyl-3-aminophenylboronic acid are added, along with 317 mg of tetrakis(triphenylphosphine)palladium. The reaction mixture is stirred for 3 hours at 90° C. The reaction is stopped by addition of 50 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 0.92 g of methyl 3-(3′-methylaminobiphenyl-4-yl)propanoate is obtained. Yield=61%

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. filtrationthe residue is then filtered on silica gel (1/1 heptane/ethyl acetate)
  5. customAfter evaporating off the solvents
  6. customthe oil obtained
  7. stirringThe reaction mixture is stirred for 3 hours at 90° C
  8. extractionextracted with ethyl acetate
  9. dry with materialdried over sodium sulfate
  10. customThe solvents are evaporated off
  11. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-85a7627c56db48bbaeb41fb01e492ab4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863332B2

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