Sodium Carbonate → 4-(5-Methyl-2-phenylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 968552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968552
Br[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:3]=1.[CH3:15][O:16][C:17]([C:19]1[N:20]([S:33]([C:36]2[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=2[CH3:44])(=[O:35])=[O:34])[CH:21]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:23]=1)=[O:18].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.C(OCC)(=O)C.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>[CH3:15][O:16][C:17]([C:19]1[N:20]([S:33]([C:36]2[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[CH:38][C:37]=2[CH3:44])(=[O:34])=[O:35])[CH:21]=[C:22]([C:2]2[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:3]=2)[CH:23]=1)=[O:18]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 590158034-Bromo-5-methyl-2-phenylpyridineHCID 59767810Methyl 1-(mesitylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 691967634-(5-Methyl-2-phenylpyridin-4-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

13 (29 mg, 0.12 mmol, 1.0 equiv.) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2,4,6-trimethylbenzensulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester (52 mg, 0.12 mmol, 1.0 equiv.) were dissolved in benzene (1.2 mL). After adding aqueous Na2CO3 (0.2 mL), Pd(PPh3)4 (28 mg, 0.024 mol, 0.2 equiv.) was then added and the resulting mixture was refluxed for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. After drying the organic layer over Na2SO4, the solvent was removed under reduced pressure. The crude product 14 was used without further purification (100 mg, HPLC Rt=7.005 minutes, ES+ 475.4, ES− not observed).

Aufarbeitung

  1. additionwas then added
  2. temperaturethe resulting mixture was refluxed for 16 hours
  3. washwashed with water
  4. dry with materialAfter drying the organic layer over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product 14 was used without further purification (100 mg, HPLC Rt=7.005 minutes, ES+ 475.4, ES− not observed)

Quellen und Nachweise

ORD-Eintrag
ord-9dfefa3017db41628b0a02164e22d89d
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304061B2

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