Sodium Carbonate → Methyl 4'-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl)[1,1'-biphenyl]-3-carboxylate

HRID 1783247

Reaktionsgleichung

Reaktionsgleichung von HRID 1783247
[CH2:1]([N:4]([CH2:26][CH2:27][CH3:28])[C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:6])[CH2:2][CH3:3].[CH3:29][N:30]([S:32]([C:35]1[CH:40]=[CH:39][C:38](Br)=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH3:31].C(=O)([O-])[O-].[Na+].[Na+]>O.C1(C)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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:29][N:30]([CH3:31])[S:32]([C:35]1[CH:36]=[CH:37][C:38]([C:15]2[CH:16]=[C:7]([C:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:26][CH2:27][CH3:28])=[O:6])[CH:8]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:14]=2)=[CH:39][CH:40]=1)(=[O:33])=[O:34]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 128184-Bromo-N,N-dimethylbenzenesulphonamideHCID 21086174Methyl 3-[(dipropylamino)carbonyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Produkt 1

HCID 69680482Methyl 4'-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl)[1,1'-biphenyl]-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

A mixture of methyl 3-[(dipropylamino)carbonyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Step 1, 534 mg, 1.4 mmol), 4-bromobenzenedimethyl-sulfonamide (363 mg, 1.4 mmol), and sodium carbonate (2 mL of a 2 M mixture in water, 4.1 mmol) in toluene (10 mL) is degassed under reduced pressure for 15 minutes and then purged with argon. Palladium tetrakis(triphenylphosphine) (40 mg, 0.025 mmol) is added and the reaction mixture is degassed under reduced pressure for 15 minutes and then purged with argon. The reaction mixture is heated at reflux for 4 hours, cooled to 20-25 degrees C., filtered through a plug of diatomaceous earth and sodium sulfate, and the filtrate is concentrated under reduced pressure. Purification by flash column chromatography (silica; ethyl acetate/hexanes, 1/1) gives methyl 4′-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylate (XXXVIII), ESI-MS (m/z) [M+H]+=447.

Aufarbeitung

  1. customis degassed under reduced pressure for 15 minutes
  2. custompurged with argon
  3. customthe reaction mixture is degassed under reduced pressure for 15 minutes
  4. custompurged with argon
  5. temperatureThe reaction mixture is heated
  6. temperatureat reflux for 4 hours
  7. filtration, filtered through a plug of diatomaceous earth and sodium sulfate
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customPurification by flash column chromatography (silica; ethyl acetate/hexanes, 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-1bcdcc36dd6d44ec80d1dda3af44d1d1
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498436B2

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