Methanol → 1H-Indole-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester

HRID 460006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460006
[C:1]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[C:14](Br)[CH:13]=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][OH:19].CN([CH:23]=[O:24])C>CCN(CC)CC.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:18][O:19][C:23]([C:14]1[C:15]2[CH:16]=[C:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:24]

Komponenten

7

Edukt 3

HCID 887MethanolHCID 6228DimethylformamideHCID 68857000tert-butyl 4-bromo-1H-indole-2-carboxylate

Produkt 1

HCID 688587391H-Indole-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 7.3 g 4-Bromo-1H-indole-2-carboxylic acid tert-butyl ester in 100 ml DMF, 6.8 ml NEt3, 276 mg Pd(OAc)2, 128 mg 1,1′-Bis(diphenylphosphino)ferrocene, 12 ml MeOH were added and purged with argon for 15 min. This solution was then purged with carbon monoxide and heated to 70° C. for 4 h. The reaction mixture was concentrated under reduced pressure, the residue dissolved in 200 ml DCM and washed with 100 ml water. The organic layer was dried over MgSO4 and, after removal of the solvent under reduced pressure, the residue was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate 9:1. The fractions containing the product were collected and concentrated under reduced pressure. Yield: 3.8 g. MS (ESI+): m/e=276.

Aufarbeitung

  1. custompurged with argon for 15 min
  2. customThis solution was then purged with carbon monoxide
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue dissolved in 200 ml DCM
  5. washwashed with 100 ml water
  6. dry with materialThe organic layer was dried over MgSO4
  7. customafter removal of the solvent under reduced pressure
  8. customthe residue was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate 9:1
  9. additionThe fractions containing the product
  10. customwere collected
  11. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6ed79dc2eecd487a8afb38aea14bb62a
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196103B2

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