Potassium Carbonate → HCID 67960634, compound

HRID 527547Notes

Reaction equation

HRID 527547 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])[C:16]2=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=[C:15]2[O:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:12]1([CH3:22])[C:16]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:15]=2[O:14][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 574112993,3-Dimethyl-2,3-dihydro-1-benzofuran-4-ol2×

Product 1

HCID 67960634HCID 67960634, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a large microwave vial, 2-chloro-5-nitropyridine (386 mg, 2.436 mmol) was dissolved in 4 ml of dimethylformamide. 3,3-dimethyl-2,3-dihydro-1-benzofuran-4-ol (Intermediate 57, 400 mg) and potassium carbonate (2.02 g, 14.62 mmol) were added. The reaction mixture was heated under microwave irradiation during 30 minutes at 110 C (Biotage Initiator). The reaction mixture was filtered. The filtrated solid was washed with dichloromethane (30 ml). The volatiles were evaporated under vacuum. The residue was purified by silica gel chromatography (Companion instrument, 120 g cartridge) with cyclohexane as eluent to afford the title compound (470 mg).

Workup

  1. temperatureThe reaction mixture was heated under microwave irradiation during 30 minutes at 110 C (Biotage Initiator)
  2. filtrationThe reaction mixture was filtered
  3. washThe filtrated solid was washed with dichloromethane (30 ml)
  4. customThe volatiles were evaporated under vacuum
  5. customThe residue was purified by silica gel chromatography (Companion instrument, 120 g cartridge) with cyclohexane as eluent

Sources & evidence

ORD record
ord-3d5e44516b464e3d8399c6a4208f3093
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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