(E)-tert-butyl 3-(6-(but-2-en-2-yl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoate → Tert-butyl 3-(6-(sec-butyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoate

HRID 1854765Notes

Reaction equation

HRID 1854765 reaction equation
[CH3:1]/[C:2](/[C:5]1[N:10]=[C:9]2[O:11][C:12]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:13]([C:14](=[O:17])[NH:15][CH3:16])[C:8]2=[CH:7][C:6]=1[C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=1)[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:3]\[CH3:4]>CCO.[Pd]>[CH:2]([C:5]1[N:10]=[C:9]2[O:11][C:12]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:13]([C:14](=[O:17])[NH:15][CH3:16])[C:8]2=[CH:7][C:6]=1[C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=1)[C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])([CH2:3][CH3:4])[CH3:1]

Participants

4

Reactant 1

HCID 90402428(E)-tert-butyl 3-(6-(but-2-en-2-yl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoate

Product 1

HCID 90402567Tert-butyl 3-(6-(sec-butyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd/C (50 mg, 0.047 mmol, 10%) was added to a stirring solution of (E)-tert-butyl 3-(6-(but-2-en-2-yl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoate (118 mg, 0.236 mmol) in EtOH (4.7 ml) at rt. The reaction was placed in a Parr bomb and charged with 50 PSI of H2 and the mixture was allowed to stir for 16 h at rt. Celite was added to the reaction mixture and the slurry was filtered through a pad of Celite washing with EtOAc. The filtrate was concentrated to give the expected product tert-butyl 3-(6-(sec-butyl)-2-(4-fluorophenyl)-3-(methylcarbamoyl)furo[2,3-b]pyridin-5-yl)benzoate (118 mg, 0.235 mmol, 100% yield) consistent by LCMS. LC-MS retention time: 2.38 min; m/z (MH+): 503. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 2 min, and an analysis time of 4 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Workup

  1. additioncharged with 50 PSI of H2
  2. additionCelite was added to the reaction mixture
  3. filtrationthe slurry was filtered through a pad of Celite
  4. washwashing with EtOAc
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-93447f7a15934654b26f3defb8729d02
Source dataset
uspto-grants-2015_02
Patent number
US08962651B2

Reaction notes

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