Water → HCID 21061947, compound

HRID 1436726Notes

Reaction equation

HRID 1436726 reaction equation
[CH2:1]([N:4]([CH2:14][CH2:15][CH3:16])[C:5]([C:7]1[CH:12]=[C:11](Cl)[CH:10]=[CH:9][N:8]=1)=[O:6])[CH2:2][CH3:3].C(N(CC)CC)C.CN([CH:27]=[O:28])C.[OH2:29]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=C(P[C-]2C=CC=C2)C=C(C)C=1.[C-]1(PC2C=C(C)C=C(C)C=2)C=CC=C1.[Fe+2]>[CH2:1]([N:4]([CH2:14][CH2:15][CH3:16])[C:5]([C:7]1[CH:12]=[C:11]([CH:10]=[CH:9][N:8]=1)[C:27]([OH:28])=[O:29])=[O:6])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 43088322HCID 43088322, compound

Product 1

HCID 21061947HCID 21061947, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 178425330HCID 178425330, compoundCatalyst

Procedure

Heat a mixture of 4-chloropyridine-2-carboxylic acid dipropylamide (1.02 g, 4.2 mmol), palladium (II) acetate (11.3 mg, 0.05 mmol), triethylamine (1.0 mL, 7.1 mmol), 1,1′-bis(3,5-dimethylphenylphosphino)ferrocene (138 mg, 0.55 mmol), DMF (35 mL) and water (5 mL) at 110° C. under an atmosphere of carbon monoxide (200 psi) overnight. Filter the reaction, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 methanol:chloroform) to give the title compound (75 mg, 7%).

Workup

  1. temperatureHeat
  2. filtrationFilter
  3. customthe reaction
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 0:100 to 10:90 methanol:chloroform)

Sources & evidence

ORD record
ord-65cd2a49db514d3c88eeeaef513466c8
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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