Glyoxylic Acid → HCID 16243946, compound

HRID 404686Notes

Reaction equation

HRID 404686 reaction equation
O=[CH:2][C:3]([OH:5])=[O:4].[NH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1B(O)O>C(#N)C>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[CH:2]([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 8082PiperidineHCID 27343342,4-Difluorophenylboronic acid

Product 1

HCID 16243946HCID 16243946, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Oxoacetic acid (141 mg, 1.90 mmol) and piperidine (0.16 ml, 1.90 mmol) were dissolved in acetonitrile (10 ml). 2,4-Difluorophenylboronic acid (300 mg, 1.90 mmol) was added and the mixture was stirred at reflux for 4 hours. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=85/25) to obtain the title compound (307 mg, 63% yield) as an off-white solid.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe solvent was evaporated
  3. customthe crude was purified by flash chromatography (DCM/MeOH=85/25)

Sources & evidence

ORD record
ord-fdad088ce98d4a00adaff2c58dceb417
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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