Formic Acid → HCID 21706673, compound

HRID 356979Notes

Reaction equation

HRID 356979 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.C(O)=O>O1CCOCC1.[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9](=[O:18])[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 53750894HCID 53750894, compound

Product 1

HCID 21706673HCID 21706673, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a slurry of Compound 1 (21.3 g, 67.4 mmol) in 1,4-dioxane (40 mL) was added triethylamine (48.1 mL, 0.346 mol), formic acid (6.54 mL, 0.145 mol) and 10% palladium on carbon (0.7 g) and the resulting mixture heated to reflux. After stirring at reflux for 1 hr, the reaction was cooled to room temperature filtered and concentrated in vacuo. The resulting residue was chromatographed over silica gel (elution with 5% methanol/methylene chloride) to provide the desired material.

Workup

  1. temperaturethe resulting mixture heated to reflux
  2. temperatureat reflux for 1 hr
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed over silica gel (elution with 5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-00dc851898a74f48b2984739db65df4d
Source dataset
uspto-grants-1998_11
Patent number
US05840736

Reaction notes

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