Diisopropylethylamine → HCID 64165463, compound

HRID 1967548Notes

Reaction equation

HRID 1967548 reaction equation
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.I[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1.[SH:50][C:51]1[CH:52]=[C:53]([CH:57]=[CH:58][CH:59]=1)[C:54]([OH:56])=[O:55].C(N(CC)C(C)C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[N:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[S:50][C:51]1[CH:52]=[C:53]([CH:57]=[CH:58][CH:59]=1)[C:54]([OH:56])=[O:55]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 95737Benzoic acid, 3-mercapto-HCID 2211262-IodopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 64165463HCID 64165463, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Xantphos (3.75 g) and Pd2(dba)3 (2.97 g) were added in that order to a dioxane (150 mL) solution of 2-iodopyridine (7.31 g), 3-mercaptobenzoic acid (5.0 g) and N,N-diisopropylethylamine (11.30 mL), and stirred overnight in a nitrogen atmosphere at 100° C. After left cooled, the reaction solution was evaporated under reduced pressure, then ethyl acetate was added to the residue, washed three times with aqueous saturated ammonium chloride solution, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (methanol/chloroform=from 0% to 20%, gradient) to give the intended product (4.95 g, 66%) as a brown solid.

Workup

  1. waitAfter left
  2. temperaturecooled
  3. customthe reaction solution was evaporated under reduced pressure
  4. additionethyl acetate was added to the residue
  5. washwashed three times with aqueous saturated ammonium chloride solution
  6. dry with materialdried with sodium sulfate
  7. customThe drying agent was removed through filtration
  8. customthe solvent was evaporated off under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (methanol/chloroform=from 0% to 20%, gradient)

Sources & evidence

ORD record
ord-1505730bec23482b9b5176690a39f9e8
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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