Potassium Carbonate → HCID 67958356, compound

HRID 527664Notes

Reaction equation

HRID 527664 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]1([CH3:22])[CH2:16][C:15]2=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=[C:14]2[O:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:12]1([CH3:22])[CH2:16][C:15]2[C:17]([O:21][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=3)=[CH:18][CH:19]=[CH:20][C:14]=2[O:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 541810862,2-Dimethyl-2,3-dihydro-1-benzofuran-4-ol

Product 1

HCID 67958356HCID 67958356, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a microwave vial, 2-chloro-5-nitropyridine (97 mg, 0.609 mmol) was dissolved in 3 mL of dimethylformamide. 2,2-dimethyl-2,3-dihydro-1-benzofuran-4-ol (100 mg, 0.609 mmol) and potassium carbonate (253 mg, 1.827 mmol) were added. The reaction mixture was heated under microwave irradiation for 1 hour at 110 C. The reaction mixture was filtered. The filtrated solid was washed with dichloromethane (5 ml). The volatiles were evaporated under vacuum. The crude compound was dissolved in dichloromethane (8 ml) and brine was added (8 ml). The compound was extracted 2 times with dichloromethane (2×8 ml) and 2 times with ethylacetate (2×8 ml). Combined organic layers were dried over sodium sulphate and evaporated. The residue was purified by silica gel chromatography (Companion system, 12 g Si cartridge) with cyclohexane/ethyl acetate from 100:0 to 80:20 as eluents affording the title compound (120 mg).

Workup

  1. temperatureThe reaction mixture was heated under microwave irradiation for 1 hour at 110 C
  2. filtrationThe reaction mixture was filtered
  3. washThe filtrated solid was washed with dichloromethane (5 ml)
  4. customThe volatiles were evaporated under vacuum
  5. dissolutionThe crude compound was dissolved in dichloromethane (8 ml)
  6. additionbrine was added (8 ml)
  7. extractionThe compound was extracted 2 times with dichloromethane (2×8 ml) and 2 times with ethylacetate (2×8 ml)
  8. dry with materialCombined organic layers were dried over sodium sulphate
  9. customevaporated
  10. customThe residue was purified by silica gel chromatography (Companion system, 12 g Si cartridge) with cyclohexane/ethyl acetate from 100:0 to 80:20 as eluents

Sources & evidence

ORD record
ord-14502cc1313d4eafb5b009149e8d8868
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…