Formic Acid → Methyl 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxybenzoate

HRID 1975418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975418
C([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[CH:15]=[C:14]2[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33])=[O:10])C1C=CC=CC=1.C(O)=O>CN(C)C=O.[Pd]>[C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[CH:15]=[C:14]2[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33])([OH:10])=[O:8]

Komponenten

5

Edukt 2

HCID 284Formic AcidHCID 10343359Methyl 4-(5-benzyloxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate

Produkt 1

HCID 9998178Methyl 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxybenzoateAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of methyl 4-(5-benzyloxycarbonyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate (41.0 g) and formic acid (40 mL) in N,N-dimethylformamide (600 mL) was treated with 10% (w/w) palladium on carbon (10 g) and shaken under hydrogen (3.45 bar) for 24 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate evaporated to give an amber solid. The solid was triturated with warm diethyl ether and filtered to afford methyl 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxybenzoate as a light gray solid (28.9 g, 88%); mp 249°-251° C.; partial NMR (250 MHz, DMSO-d6): 3.78 (s, 3H, NCH3), 3.64 (s, 3H, CO2CH3), 3.93 (s, 3H, OCH3), 4.09 (s, 2H, CH2), 7.12 (s, 1H, indole-H(2)), 8.16 (s, 1H, indole-H(4)), 12.44 (br, 1H, CO2H).

Aufarbeitung

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate evaporated
  3. customto give an amber solid
  4. customThe solid was triturated with warm diethyl ether
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-1465064e38c746509473c81f8031341e
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05286740

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