Formic Acid → HCID 19012084, compound

HRID 1917094Notes

Reaction equation

HRID 1917094 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15](=[O:23])[N:16]([CH3:22])[C:17](=[O:21])[N:18]([CH3:20])[CH:19]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)=O>C(O)(=O)C.[Pd]>[CH3:20][N:18]1[CH:19]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:15](=[O:23])[N:16]([CH3:22])[C:17]1=[O:21]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 58269808HCID 58269808, compound

Product 1

HCID 19012084HCID 19012084, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

2.6 g (8.26 mmol) of compound 13a are placed in the presence of 1.3 g of palladium and of 130 mL of formic acid in 300 mL of acetic acid at room temperature for 4 h. The mixture is heated to 100° C.° for 2 h 30 min. After neutralization with a 10% soda solution, the reaction medium is extracted with CHCl3. The organic phase is washed with water and then with a saturated NaCl solution. After drying on MgSO4, the organic phase is concentrated. The obtained residue is purified by flash chromatography (CH2Cl2-MeOH—NH4OH, gradient 90-10-0 to 90-9-1 over 30 min). 1.05 g of intermediate 13b is obtained as a beige solid (yield: 56%).

Workup

  1. extractionAfter neutralization with a 10% soda solution, the reaction medium is extracted with CHCl3
  2. washThe organic phase is washed with water
  3. customAfter drying on MgSO4
  4. concentrationthe organic phase is concentrated
  5. customThe obtained residue is purified by flash chromatography (CH2Cl2-MeOH—NH4OH, gradient 90-10-0 to 90-9-1 over 30 min)

Sources & evidence

ORD record
ord-77568773b1d84d5b865391793e259f08
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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