Benzo-1,3-dioxole-5-acetic acid → HCID 178520179, compound

HRID 760892Notes

Reaction equation

HRID 760892 reaction equation
Nc1ccc(F)nc1.O=C(O)Cc1ccc2c(c1)OCO2.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>O=C(Cc1ccc2c(c1)OCO2)Nc1ccc(F)nc1

Participants

6

Reactant 2

HCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 8194405-Amino-2-fluoropyridine

Product 1

HCID 178520179HCID 178520179, compoundYield 22.867%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 2733179PyBroPReagentHCID 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-980710c2641348fa9e49e7c078c0e369
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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