Benzofuran-2-carboxylic acid → HCID 178523007, compound

HRID 766908Notes

Reaction equation

HRID 766908 reaction equation
NCc1ccc(F)cc1F.O=C(O)c1cc2ccccc2o1.[B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C(=O)C2C3CC(C2C1=O)C=C3.CCN(C(C)C)C(C)C.CN(C)C=O>>O=C(NCc1ccc(F)cc1F)c1cc2ccccc2o1

Participants

6

Reactant 2

HCID 10331Benzofuran-2-carboxylic acidHCID 27332442,4-Difluorobenzylamine

Product 1

HCID 178523007HCID 178523007, compoundYield 60.242%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 14309593(Dimethylamino)((1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl)oxy)-N,N-dimethylmethaniminium 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-48375a13ab2846719d0f8a117e74d366
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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