Potassium Carbonate → Ethyl acetate hexane

HRID 1176053Notes

Reaction equation

HRID 1176053 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([NH2:9])[NH:7][N:8]=2)[CH2:3][CH2:2]1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]([Cl:20])[N:12]=1.[C:21](=[O:24])([O-])[O-:22].[K+].[K+]>C(#N)C>[C:21]([O:22][CH2:5][CH3:6])(=[O:24])[CH3:11].[CH3:3][CH2:2][CH2:1][CH2:4][CH2:5][CH3:6].[Cl:20][C:13]1[N:12]=[C:11]([NH:9][C:6]2[NH:7][N:8]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[CH:5]=2)[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 852392,6-Dichloro-3-nitropyridineHCID 178507266HCID 178507266, compound

Product 2

HCID 21226206Ethyl acetate hexaneYield 85.4%HCID 178526632HCID 178526632, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 5-cyclopropyl-2H-pyrazol-3-ylamine (638 mg, 5.18 mmol) in 6 ml of acetonitrile was added dropwise over 10 minutes to a cooled (0 C) mixture of 2,6-dichloro-3-nitro-pyridine (1.0 g, 5.18 mmol) and potassium carbonate (860 mg, 6.22 mmol) in 20 ml of acetonitrile. After the addition, the reaction was warmed to room temperature and stirred for 18 hours. The reaction was filtered and the filtrate evaporated in vacuo to afford a brown residue which was purified by flash chromatography (SiO2) eluting with ethyl acetate-hexane (1:7) 257 mg (17.7% yield) of the desired product (major regioisomer). HPLC Rt 6.09, mins. MS: m/z 280.0 (M+1) 278.1 (M−1).

Workup

  1. temperaturea cooled
  2. additionAfter the addition
  3. filtrationThe reaction was filtered
  4. customthe filtrate evaporated in vacuo
  5. customto afford a brown residue which
  6. customwas purified by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-9ec2b19df3984dfc8b8a1cd051185d80
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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