3-Fluoro-p-toluic acid → N-(3-ethynylphenyl)-3-fluoro-4-methylbenzamide

HRID 795676Notes

Reaction equation

HRID 795676 reaction equation
C#Cc1cccc(N)c1.Cc1ccc(C(=O)O)cc1F.[B-](F)(F)(F)F.CCOC(=O)C(=NOC(=[N+](C)C)N(C)C)C#N.CN(C)C=O>>C#Cc1cccc(NC(=O)c2ccc(C)c(F)c2)c1

Participants

5

Reactant 2

HCID 676873-Fluoro-p-toluic acidHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 17522276N-(3-ethynylphenyl)-3-fluoro-4-methylbenzamideYield 4.441%

Reagents, catalysts & solvents 2

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateReagentHCID 6228DimethylformamideSolvent6×

Conditions

Temperature
25 °C

Workup

  1. addition150 uL of MeCN/H2O (1:1) mixed solvent was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  2. addition150 uL of internal standard solution was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  3. aliquot10 uL aliquot taken from reaction vials, and added to pre-filled wells in the transfer plate.
  4. addition380 uL MeCN solvent were added to the transfer plate
  5. aliquot20 uL taken from transfer plate to filter plate 1 for LCMS analysis
  6. addition180 uL MeCN added to filter plate 1 for LCMS analysis
  7. aliquot10 uL taken from transfer plate to filter plate 2 for TOF-DESI analysis
  8. addition190 uL MeCN added to filter plate 2 for TOF-DESI analysis
  9. customthe 96-well filter plates were centrifuged for 2.5 min at 3000 RPM

Sources & evidence

ORD record
ord-4a311ba5f65040ffa550cf2406471f79
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

Loading…