HCID 71246043, compound → HCID 71246306, compound

HRID 573984Notes

Reaction equation

HRID 573984 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[C:15]([N+:21]([O-])=O)[C:16]([O:19][CH3:20])=[N:17][CH:18]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[C:15]([NH2:21])[C:16]([O:19][CH3:20])=[N:17][CH:18]=2)[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 71246043HCID 71246043, compound

Product 1

HCID 71246306HCID 71246306, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

A suspension of 5-(1-benzyl-1H-pyrazol-4-yl)-2-methoxy-3-nitropyridine (Preparation 8a, 3.5 g, 11.28 mmol) in acetic acid (50 mL) was added to a cooled (10° C.) suspension of zinc (3.67 g, 56.25 g) in acetic acid (50 mL) and the resulting mixture was stirred at ambient temperature for 1.5 hours. The mixture was filtered and the solid washed with methylene chloride (50 mL). The combined filtrate and washings were evaporated and the residue was purified by flash chromatography (20-40% ethyl acetate in hexanes) to give a brown oil which was treated with a 1:1 mixture of hexanes/diethyl ether (40 mL). The resulting solid was filtered, washed with hexane and dried to yield the title compound (2.33 g, 74%) as a beige solid.

Workup

  1. additionwas added to
  2. temperaturea cooled
  3. filtrationThe mixture was filtered
  4. washthe solid washed with methylene chloride (50 mL)
  5. customThe combined filtrate and washings were evaporated
  6. customthe residue was purified by flash chromatography (20-40% ethyl acetate in hexanes)
  7. customto give a brown oil which
  8. filtrationThe resulting solid was filtered
  9. washwashed with hexane
  10. customdried

Sources & evidence

ORD record
ord-b79cb2a6e562403194086f0bfec8439f
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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