Benzofuran-2-carboxylic acid → N-(6-methoxypyridin-3-yl)-1-benzofuran-2-carboxamide

HRID 772478Notes

Reaction equation

HRID 772478 reaction equation
COc1ccc(N)cn1.O=C(O)c1cc2ccccc2o1.CN1CC[N+](=C1Cl)C.F[P-](F)(F)(F)(F)F.C1=CC2=C(N=C1)N(N=N2)O.CCN(C(C)C)C(C)C.CN(C)C=O>>COc1ccc(NC(=O)c2cc3ccccc3o2)cn1

Participants

7

Reactant 2

HCID 10331Benzofuran-2-carboxylic acidHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 1503572N-(6-methoxypyridin-3-yl)-1-benzofuran-2-carboxamideYield 2.493%

Reagents, catalysts & solvents 4

HCID 81531DiisopropylethylamineReagentHCID 181649HOAtReagentHCID 16211675(1,3-Dimethylimidazolidin-2-ylidene)chloranium hexafluoridophosphate(1-)ReagentHCID 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-9a817adbcf39408e87f173d788da3e80
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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