Acetic Acid → HCID 57516208, compound

HRID 539779Notes

Reaction equation

HRID 539779 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[F:23])=[N:13][N:12]3[CH:24]=2)=[CH:5][C:4]=1[N+:25]([O-])=O)#[CH:2].CC(O)=O>C(O)C.O.[Fe]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[F:23])=[N:13][N:12]3[CH:24]=2)=[CH:5][C:4]=1[NH2:25])#[CH:2]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 86667855HCID 86667855, compound

Product 1

HCID 57516208HCID 57516208, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-ethynyl-3-nitrophenyl)-6-(2-fluorophenyl)imidazo[1,2-b]pyridazine (0.050 g, 0.139 mmol) in ethanol (3 mL) and water (1 mL) containing AcOH (0.834 mmol) is added iron (0.038 g, 0.695 mmol). The mixture is stirred and heated at 80° C. for 2 hours, then concentrated under reduced pressure and sat. aqueous NaHCO3 (20 mL) is added. The mixture is extracted with EtOAc (3×20 mL). Organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude product is purified via chromatography using a gradient of hexanes to EtOAc to afford the title compound (0.033 g, 73%) as a yellow solid: Rf 0.30 (1:1 EtOAc:hexanes); LCMS (m/z)=329.4 [M+H]+, tR=2.65 min. (compound same as Example 320)

Workup

  1. concentrationconcentrated under reduced pressure and sat. aqueous NaHCO3 (20 mL)
  2. additionis added
  3. extractionThe mixture is extracted with EtOAc (3×20 mL)
  4. customOrganic layer is collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude product is purified via chromatography

Sources & evidence

ORD record
ord-8009d59dbad74cc5b9c8a24e7940a0b1
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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