Potassium Carbonate → HCID 67217886, compound

HRID 450568Notes

Reaction equation

HRID 450568 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[O:18]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.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:18]1[CH:22]=[CH:21][C:20]([C:2]2[N:7]=[C:6]([O:8][CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=2)=[CH:19]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734358Furan-3-boronic acidHCID 61286363HCID 61286363, compound

Product 1

HCID 67217886HCID 67217886, compoundYield 67.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

A solution of 6-chloro-3-nitro-2-(tetrahydro-2H-pyran-4-yloxy)pyridine (0.259 g, 1.00 mmol), furan-3-boronic acid (0.123 g, 1.10 mmol), tetrakis(triphenylphosphine)palladium (0) (0.058 g, 0.05 mmol) and potassium carbonate (0.276 g, 2.00 mmol) in 1,4-dioxane/water (5 mL, 4:1) was de-gassed with nitrogen and then heated at 80° C. for 18 hours. The reaction mixture was diluted with EtOAc, washed with water and brine. The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was triturated with n-hexane to afford the title compound as an off-white solid (0.197 g, 66%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-c92f86d3791644299cca7f6fa6f7a568
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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