Pyridine → Methyl 5-amino-1H-indole-3-carboxylate

HRID 970039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970039
ClC1C(C)=C(S(Cl)(=O)=O)C=CC=1.N1C=CC=C[CH:14]=1.COC([C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([NH2:32])=[CH:27][CH:26]=2)=O.[C:33]([O-:36])(O)=[O:34].[Na+]>ClCCl>[CH3:14][O:36][C:33]([C:31]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([NH2:32])[CH:29]=2)[NH:24][CH:23]=1)=[O:34]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 10330149Methyl 5-amino-1H-indole-2-carboxylate

Produkt 1

HCID 45089221Methyl 5-amino-1H-indole-3-carboxylateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (124 mg, 0.552 mmol) in dichloromethane (4 mL) was added pyridine (100 μL, 1.3 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-1H-indole-carboxylic acid methyl ester (100 mg, 0.526 mmol) was added. The resulting mixture was stirred for 1.5 h at room temperature, then saturated NaHCO3 solution (15 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (129 mg, 65%), single spot at Rf 0.84 (ethyl acetate). mp 216.8-219.3° C., [22], HPLC purity 99+% (tR 2.07 min in 10% water-acetonitrile). 1H NMR (d6-DMSO): δ 11.91 (1H, s), 10.32 (1H, s), 8.03 (1H, d, J=3.0 Hz), 7.82 (1H, d, J=7.9 Hz), 7.70-7.67 (2H, m), 7.37-7.31 (2H, m), 6.95 (1H, dd, J=8.6, 2.0 Hz), 3.77 (3H, s), 2.65 (3H, s). LCMS: 377.09. FAB-MS (MH+, C17H15ClN2O4S): calcd 378.0441, found 378.0439.

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 1.5 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (20 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-b506dcf555d543bf9e720d586a62ed26
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07309715B2

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