Water → HCID 21062077, compound

HRID 1436728Notes

Reaction equation

HRID 1436728 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][N:16]=1)[C:5]([N:7]([CH2:11][CH2:12][CH3:13])[CH2:8][CH2:9][CH3:10])=[O:6].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]>[CH2:8]([N:7]([CH2:11][CH2:12][CH3:13])[C:5]([C:4]1[CH:14]=[CH:15][N:16]=[C:2]([C:27]([OH:28])=[O:29])[CH:3]=1)=[O:6])[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 28376001HCID 28376001, compound

Product 1

HCID 21062077HCID 21062077, compoundYield 51%

Reagents, catalysts & solvents 2

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

Procedure

Heat a mixture of 2-chloro-N,N-dipropylisonicotinamide (0.91 g, 3.8 mmol), palladium (II) acetate (13.2 mg), triethylamine (1.0 mL, 7.1 mmol), 1,1′-bis(3,5-dimethylphenylphosphino)ferrocene (161 mg, 0.64 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 (486 mg, 51%).

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-f40165d7179d45bcbe4fff1859285a4a
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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