HCID 131734939, compound → HCID 131734938, compound

HRID 921846Notes

Reaction equation

HRID 921846 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([CH2:10][OH:11])=[CH2:9])=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]>CCO.[Pd]>[Cl:1][C:2]1[C:7]([CH:8]([CH3:9])[CH2:10][OH:11])=[CH:6][C:5]([C:12]#[N:13])=[CH:4][C:3]=1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 131734939HCID 131734939, compound

Product 1

HCID 131734938HCID 131734938, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl (2-chloro-5-cyano-3-(3-hydroxyprop-1-en-2-yl)phenyl)carbamate (161 mg, 0.521 mmol) was taken up in EtOH (3 mL) and the solution was purged with N2. Next, Pd/C (55.5 mg, 0.052 mmol) was added and the solution was again evacuated and purged with N2 3×. Next, a balloon with H2 was added, and the reaction was stirred for 1 h. The reaction mixture was filtered through celite, rinsing with MeOH. The solvent was removed in vacuo and the material was purified by flash column chromatography (0-50% EtOAc/Hex; 40 g column). Tert-butyl (2-chloro-5-cyano-3-(1-hydroxypropan-2-yl)phenyl)carbamate (36 mg) was obtained as a colorless glass.

Workup

  1. customthe solution was purged with N2
  2. customthe solution was again evacuated
  3. custompurged with N2 3×
  4. additionNext, a balloon with H2 was added
  5. filtrationThe reaction mixture was filtered through celite
  6. washrinsing with MeOH
  7. customThe solvent was removed in vacuo
  8. customthe material was purified by flash column chromatography (0-50% EtOAc/Hex; 40 g column)

Sources & evidence

ORD record
ord-e446f92f16dc4429b9c97f9185bc4288
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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