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

HRID 1741902Notes

Reaction equation

HRID 1741902 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 9998178Methyl 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxybenzoateYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6344d10b25634c6d8412be43aa315eb4
Source dataset
uspto-grants-1994_08
Patent number
US05334765

Reaction notes

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