Ammonium formate → HCID 67315438, compound

HRID 1254137Notes

Reaction equation

HRID 1254137 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8](=[C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=4)[NH:15][C:14]3=[O:23])[O:9][CH:10]([CH2:11][CH3:12])[C:4]=2[CH:3]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:11]([CH:10]1[C:4]2[CH:3]=[CH:2][N:7]=[CH:6][C:5]=2[C:8](=[C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[NH:15][C:14]2=[O:23])[O:9]1)[CH3:12]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 76798886HCID 76798886, compound

Product 1

HCID 67315438HCID 67315438, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(6-Chloro-1-ethyl-1H-furo[3,4-c]pyridin-3-ylidene)-5-fluoro-1,3-dihydro-indol-2-one (50 mg, 0.15 mmol) in 8 ml ethanol is treated with 50 mg of 5% Pd/C and ammonium formate (500 mg). The reaction mixture is stirred for 24 h at room temperature. The reaction mixture is concentrated and is then loaded onto silica gel and purified using 5% MeOH-EtOAc. The product containing fractions are concentrated to give the title compound (18 mg, 40%).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. custompurified
  3. additionThe product containing fractions
  4. concentrationare concentrated

Sources & evidence

ORD record
ord-530a6a1d26c5494e96c03b62d80e12e3
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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