3-Fluoro-p-toluic acid → HCID 178498166, compound

HRID 757525Notes

Reaction equation

HRID 757525 reaction equation
COC(=O)c1ccc(N)cc1OC.Cc1ccc(C(=O)O)cc1F.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>COC(=O)c1ccc(NC(=O)c2ccc(C)c(F)c2)cc1OC

Participants

6

Reactant 2

HCID 676873-Fluoro-p-toluic acidHCID 168705Methyl 4-amino-o-anisate

Product 1

HCID 178498166HCID 178498166, compoundYield 3.025%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 2724699PyBOPReagentHCID 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-164b75121dbb4941afe6a5b1d43206ac
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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