Pyridine → HCID 59026806, compound

HRID 658380Notes

Reaction equation

HRID 658380 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([NH:7][NH:8][C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[F:25])=[O:10])=O)[CH3:2].N1C=CC=CC=1.S(Cl)(Cl)=O.CCOC(C)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:5]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])=[N:8][N:7]=1)=[O:26])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 69457730HCID 69457730, compound

Product 1

HCID 59026806HCID 59026806, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of {N′-[3-(2-Fluoro-4-iodo-phenylamino)-pyridine-4-carbonyl]-hydrazino}-oxo-acetic acid ethyl ester (1.27 g, 2.69 mmol, 1.0 eq.) in DCM (20 mL) containing pyridine (0.55 g, 6.99 mmol. 2.66 eq.) thionyl dichloride (0.26 mL, 3.5 mmol; 1.30 eq) was added at 0° C. The reaction mixture were stirred at 0° C. for 2 hrs. The solvent was evaporated, toluene was added and the reaction mixture was stirred at 110° C. for 6 hrs. Removal of the solvent resulted in a residue that was subjected to silica gel column chromatography (EtOAc:Hex=1:2) to afford the desired product (0.50 g). [5.32 min; 455 (M+1)]

Workup

  1. additionwas added at 0° C
  2. customThe solvent was evaporated
  3. additiontoluene was added
  4. stirringthe reaction mixture was stirred at 110° C. for 6 hrs
  5. customRemoval of the solvent
  6. customresulted in a residue that

Sources & evidence

ORD record
ord-d20f5f4298cf4c5eb6cad6418093d308
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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