Nitrogen → HCID 58710056, compound

HRID 2375903Notes

Reaction equation

HRID 2375903 reaction equation
N#N.I[C:4]1[C:5](=[O:14])[N:6]([CH3:13])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1.[S:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C([O-])(=O)C.[K+]>CN(C=O)C.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>[CH3:13][N:6]1[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=[C:4]([C:19]2[S:15][CH:16]=[N:17][CH:18]=2)[C:5]1=[O:14]

Participants

7

Reactant 4

HCID 947NitrogenHCID 9256ThiazoleHCID 517044Potassium AcetateHCID 13567769HCID 13567769, compound

Product 1

HCID 58710056HCID 58710056, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

N2 was bubbled through a solution of 3-iodo-1-methyl-5-nitro-1H-pyridin-2-one (840 mg, 3.0 mmol), thiazole (1280 mg, 15.0 mmol), potassium acetate (0.883 g, 9.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.243 g, 0.21 mmol) in DMF (8 mL) for 10 min. The mixture was then heated to 120° C. and stirred for 28 h. The solvents were removed in vacuo. The black-colored residue was dissolved in a mixture of methanol (8 mL) and methylene chloride (250 mL). Water (30 mL) and sat. NaHCO3 (aq) (15 mL) were added. Layers were separated and the aqueous phase was extracted with methylene chloride (3×80 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated under reduced pressure to 15 mL. The product precipitated and was collected by filtration to afford the desired product as a black solid. 1H-NMR (DMSO-d6, 400 MHz): δ=3.70 (s, 3H), 8.79 (s, 1H), 8.82 (d, J=2.8 Hz, 1H), 9.13 (s, 1H), 9.29 (d, J=3.2 Hz, 1H). MS (ES+): m/z 238.15 [MH+]. HPLC: tR=2.33 min (ZQ2000, polar—5 min).

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionThe black-colored residue was dissolved in a mixture of methanol (8 mL) and methylene chloride (250 mL)
  3. additionWater (30 mL) and sat. NaHCO3 (aq) (15 mL) were added
  4. customLayers were separated
  5. extractionthe aqueous phase was extracted with methylene chloride (3×80 mL)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure to 15 mL
  9. customThe product precipitated
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-8b034e9c254a482581dca34d454378a8
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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