Sodium Carbonate → 4-(1H-Indol-6-YL)benzoic acid

HRID 1785744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1785744
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.OB(O)[C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.CN(C=O)C>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=3)[CH:10]=2)[CH:6]=[CH:7]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 6764936-Bromoindole

Produkt 1

HCID 227303814-(1H-Indol-6-YL)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6-bromoindole (480 mg, 2.45 mmol), 4-(dihydroxyboryl)benzoic acid (406 mg, 2.45 mmol), Pd(dppf)Cl2CH2Cl2 (10 mg, 0.01 mmol), and 2M Na2CO3 (5.6 mL, 11.2 mmol) in a mixture of ethanol (4 mL) and DMF (7 mL) was heated to 100° C., stirred for 16 hours, filtered, and concentrated The concentrate was dissolved in ethyl acetate, washed sequentially with 1M H3PO4, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane to provide the desired product. MS (ESI(−)) m/e 236 (M−H)−.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated The concentrate
  3. dissolutionwas dissolved in ethyl acetate
  4. washwashed sequentially with 1M H3PO4, water, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with 5% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-564003229d9d4c2b99027e9f3ba45c3d
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504512B2

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