Potassium Carbonate → HCID 67966839, compound

HRID 527596Notes

Reaction equation

HRID 527596 reaction equation
[CH3:1][C:2]12[CH2:12][CH:11]1[C:10]1[C:9]([OH:13])=[CH:8][CH:7]=[CH:6][C:5]=1[O:4][CH2:3]2.C([O-])([O-])=O.[K+].[K+].Cl[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=1>CN(C)C=O>[CH3:1][C:2]12[CH2:12][CH:11]1[C:10]1[C:9]([O:13][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=3)=[CH:8][CH:7]=[CH:6][C:5]=1[O:4][CH2:3]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 67966831HCID 67966831, compound2×

Product 1

HCID 67966839HCID 67966839, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1a-methyl-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-7-ol (Intermediate 125, 190 mg) in dry N,N-dimethylformamide (10 ml) were added K2CO3 (447 mg, 3.23 mmol) and 2-chloro-5-nitropyridine (171 mg, 1.078 mmol) to give a light brown solution. The reaction was heated at 110° C. for 1 hour and then quenched with water, extracted with ethyl acetate, washed with brine, dried over sodium sulphate, filtered and concentrated under vacuum. The residue obtained was purified by silica gel chromatography (Companion system, with a gradient from pure Cyclohexane to cyclohexane/ethyl acetate 5/1) to give the title compound as a light brown solid (250 mg).

Workup

  1. customto give a light brown solution
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue obtained
  9. customwas purified by silica gel chromatography (Companion system

Sources & evidence

ORD record
ord-fa6951382900459c896df600c1c658d2
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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