2,6-Lutidine → HCID 178444624, compound

HRID 1813052Notes

Reaction equation

HRID 1813052 reaction equation
C#CCCCCC=O.c2ccccc2c1ccc(C(=O)CBr)cc1>NC(=O)C1CCCN1.FC1=CC([Ir]C2=C(C3=NC=CC=C3)C(F)=CC(F)=C2)=C(C4=NC=CC=C4)C(F)=C1.FC5=CC(F)=CC=C5C6=NC=CC=C6.CN(C)C=O.Cc1cccc(C)n1>C#CCCC[C@@H](C=O)CC(=O)c1ccc(-c2ccccc2)cc1.C#CCCC[C@H](C=O)CC(=O)c1ccc(-c2ccccc2)cc1

Participants

8

Reactant 3

HCID 79372,6-LutidineHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanoneHCID 11355455Hept-6-ynal

Product 2

HCID 178444624HCID 178444624, compoundHCID 178444625HCID 178444625, compound

Reagents, catalysts & solvents 3

HCID 550774Pyrrolidine-2-carboxamideCatalystHCID 178505915HCID 178505915, compoundCatalystHCID 6228DimethylformamideSolvent5×

Conditions

Temperature
22 °C

Workup

  1. aliquot4 uL mixture of each reacted solution was collected and diluted with 36 uL ACN
  2. addition4 uL mixture of each reacted solution was collected and diluted with 36 uL ACN
  3. additionchiral resolving regent (150 mM in DCM, 40 uL)
  4. additionCuI with DIPEA (400 mM in ACN) 40 uL
  5. additioninternal standard 1-phenylprop-2-yn-1-ol (4) (25 mM in ACN) 40 uL
  6. stirringNo procedure recorded
  7. aliquotAfter the reaction, 10 uL of supernatant for each reaction was transferred to another 96-well plate
  8. additionAfter the reaction, 10 uL of supernatant for each reaction was transferred to another 96-well plate and diluted with 190 uL ACN before the IM-MS analysis

Sources & evidence

ORD record
ord-6df96b296c2a436ab3d1772479ac46d6
Source dataset
Dataset from `Ultra-high-throughput mapping of the chemical space of asymmetric catalysis enables accelerated reaction discovery`

Reaction notes

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