Dimethylformamide → HCID 59594537, compound

HRID 2262682Notes

Reaction equation

HRID 2262682 reaction equation
[Cl:1][C:2]1[C:3](I)=[C:4]([F:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:11][N:12](C=O)C.CCOC(C)=O>[Cl-].[Na+].O.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:5]1[C:4]([F:9])=[C:3]([C:2]([Cl:1])=[CH:7][N:6]=1)[C:11]#[N:12]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 595945415-Chloro-3-fluoro-4-iodo-2-pyridinamine

Product 1

HCID 59594537HCID 59594537, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
175 °C

Procedure

To a 200 mL round bottom flask was added 5-chloro-3-fluoro-4-iodopyridin-2-amine (9.7 g, 5.5 mmol, 1.0 equiv), zinc cyanide (4.6 g, 6.1 mmol), tetrakis(triphenylphosphine)palladium(0) (4.1 g, 0.56 mmol), and DMF (80 mL). The reaction mixture was heated to 175° C. for 40 minutes. The reaction was then poured into a mixture of EtOAc (300 mL) and brine (150 mL). The organic layer was separated, washed with brine (150 mL), dried over Na2SO4, and concentrated. The residue was dissolved in CH2Cl2 and purified by silica gel chromatography (5-30% EtOAc/hexanes) to yield 4.1 g of the title compound (69%) as an off-white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (150 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. custompurified by silica gel chromatography (5-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-863cda564ce34f4d92060906766a79a1
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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