Potassium Carbonate → HCID 66784289, compound

HRID 1020859Notes

Reaction equation

HRID 1020859 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16]([C:18]1[CH:23]=[C:22]([N+]([O-])=O)[CH:21]=[CH:20][N:19]=1)[CH3:17]>CS(C)=O>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][C:22]2[CH:21]=[CH:20][N:19]=[C:18]([CH2:16][CH3:17])[CH:23]=2)=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol2×HCID 22392577HCID 22392577, compound

Product 1

HCID 66784289HCID 66784289, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-fluoro-4-bromophenol (0.576 ml, 5.258 mmol) in DMSO (8 ml) was added K2CO3 (1.451 g, 10.516 mmol) and 2-ethyl-4-nitropyridine [CAS. 101860-96-2] (0.800 g, 5.258 mmol). The reaction mixture was heated at 100° C. for 2 days. Then the reaction mixture was refilled with 2-fluoro-4-bromophenol (0.115 ml) and heated at 100° C. for 6 hours more. After cooling to r.t. the reaction mixture was washed with NaHCO3 (aqueous sat. solution), then extracted with DCM. The organic layer was separated, dried (Na2SO4) evaporated to dryness. The crude product was purified by column chromatography (silica gel; DCM to heptane/DCM from 100/0 to 30/70 as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D55 (0.985 g, 63%).

Workup

  1. temperatureheated at 100° C. for 6 hours more
  2. temperatureAfter cooling to r.t. the reaction mixture
  3. washwas washed with NaHCO3 (aqueous sat. solution)
  4. extractionextracted with DCM
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customThe crude product was purified by column chromatography (silica gel; DCM to heptane/DCM from 100/0 to 30/70 as eluent)
  9. customThe desired fractions were collected
  10. concentrationconcentrated in vacuo
  11. customto yield intermediate compound D55 (0.985 g, 63%)

Sources & evidence

ORD record
ord-ee2f920496c94df7b260481ed0101f4d
Source dataset
uspto-grants-2014_05
Patent number
US08716480B2

Reaction notes

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