Ammonium formate → HCID 18926567, compound

HRID 1600188Notes

Reaction equation

HRID 1600188 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])=[CH:13][CH:14]=2)[C:9]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:8]1[CH3:28])=[O:4].C([O-])=O.[NH4+]>[Pd].CO.O1CCCC1>[C:18]([CH2:17][CH2:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C:8]([CH3:28])=[C:9]2[CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([OH:20])=[O:19]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 18926589HCID 18926589, compound

Product 1

HCID 18926567HCID 18926567, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (E)-3-[1-(2-methoxycarbonylethyl)-2-methyl-3-(3-pyridylmethyl)-1H-indol-5-yl]-2-propenoic acid (2.02 g), 10% palladium on carbon (0.20 g) and ammonium formate (1.68 g) in methanol (20 ml) and tetrahydrofuran (20 ml) was heated at 60° C. for 4 hours and then cooled and filtered. The residue was washed with methanol, and the filtrate and washings were combined and evaporated. The residue was triturated with dilute acetic acid to give a gummy solid. The solid was filtered off and boiled with ether to give the title compound as a crystalline solid (1.79 g), m.p. 144°-146° C. Found: C,69.60; H,6.20; N,7.16. C22 H24N2O4 requires: C,69.45; H,6.36; N,7.37%.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe residue was washed with methanol
  4. customevaporated
  5. customThe residue was triturated with dilute acetic acid
  6. customto give a gummy solid
  7. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-bdcd2a3482a74407b9d19d32e7315b6a
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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