HCID 67314789, compound → HCID 67314740, compound

HRID 1011354Notes

Reaction equation

HRID 1011354 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH:21]=[CH:22][O:23][CH3:24])=[CH:18][CH:19]=2)[CH2:14][O:13]1>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH2:21][CH2:22][O:23][CH3:24])=[CH:18][CH:19]=2)[CH2:14][O:13]1

Participants

4

Reactant 1

HCID 67314789HCID 67314789, compound

Product 1

HCID 67314740HCID 67314740, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-fluoro-3-[2-(2-methoxy-vinyl)-7H-furo[3,4-b]pyridin-5-ylidene]-1,3-dihydro-indol-2-one (27 mg, 0.08 mmol) in 10 mL MeOH is treated with palladium (10% on activated carbon, 27 mg) under an argon atmosphere. The resulting mixture is subject to hydrogenation at a pressure of 35 psi for 12 h. The reaction mixture is filtered, concentrated, and the residue is chromatographed (silica gel, MeOH-Chloroform). The product containing fractions are concentrated to give the title compound as yellow solid (5 mg, 18%).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated
  3. customthe residue is chromatographed (silica gel, MeOH-Chloroform)
  4. additionThe product containing fractions
  5. concentrationare concentrated

Sources & evidence

ORD record
ord-7127c8de7b3a42a0b7ad0ff1f1aae747
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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