Hydrochloric Acid → HCID 178526834, compound

HRID 1620100Notes

Reaction equation

HRID 1620100 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].O[C:8]1[C:13](I)=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][N:9]=1.Cl.CN(C)[C:21](=O)[CH3:22]>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.O.O1CCOCC1>[OH:4][C:1]1[C:13]([CH:8]2[CH2:22][CH2:21]2)=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][N:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 178526840HCID 178526840, compound

Product 1

HCID 178526834HCID 178526834, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Cesium carbonate (3.6 g), cyclopropylboronic acid•monohydrate (1.0 g), tetrakis(triphenylphosphine)palladium (0.87 g), and water (0.2 ml) were added to a 1,4-dioxane (20 ml) solution containing 2-hydroxy-3-iodo-5-nitropyridine (2.00 g) in a nitrogen atmosphere, followed by stirring for 10 hours. Then, N,N-dimethylacetamide (10 ml) was added to the reaction solution, followed by stirring at 120° C. for 7.5 hours. The reaction solution was adjusted to room temperature and the pH was adjusted to pH 2 with the addition of water and 6M hydrochloric acid, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1 to 0:1), and a white solid of 2-hydroxy-5-nitro-3-cyclopropylpyridine (0.41 g) was thus obtained.

Workup

  1. stirringby stirring at 120° C. for 7.5 hours
  2. customwas adjusted to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1 to 0:1)

Sources & evidence

ORD record
ord-25117a7714414ba7a2e90d02e5fa75e2
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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