Potassium Carbonate → HCID 86700867, compound

HRID 881760Notes

Reaction equation

HRID 881760 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:12][CH:11]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C:37]1[CH2:42][CH2:41][C:40]([C:48]([O:50][CH2:51][CH3:52])=[O:49])([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:39][CH:38]=1)(=O)=O>O1CCOCC1.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>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:37]3[CH2:42][CH2:41][C:40]([C:43]([O:45][CH2:46][CH3:47])=[O:44])([C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH2:39][CH:38]=3)=[CH:14][CH:15]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 86692328HCID 86692328, compoundHCID 86700866HCID 86700866, compound

Product 1

HCID 86700867HCID 86700867, compoundYield 61.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A flask was charged with 5-nitro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (3.9 g, 10.73 mmol) and potassium carbonate (6.77 g, 48.3 mmol) in dioxane (60 ml) and Water (25 ml), and stirred at room temperature for 10 minutes under nitrogen. Then Pd(PPh3)4 (1.240 g, 1.073 mmol) and diethyl 4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-ene-1,1-dicarboxylate (4.22 g, 11.27 mmol) were added to the reaction mixture. The flask was sealed, flushed with nitrogen for three times and heated at 100° C. for 1 hour. The organic solvent was evaporated under vacuum and EtOAc (3×100 ml) was used to extract and the combined organic solvent was washed by saturated aqueous sodium bicarbonate solution, brine, and dried over Na2SO4, then concentrated. The residue was purified by flash chromatography (heptanes/acetone 1/2) to afford diethyl 4′-(5-nitropyridin-2-yl)-5,6-dihydro-[1,1′-biphenyl]-4,4(3H)-dicarboxylate (2.8 g, 61%) as yellow solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.25 (t, J=7.20 Hz, 6H) 2.30 (dt, J=6.28, 3.24 Hz, 2H) 2.53 (dd, J=4.67, 1.77 Hz, 2H) 2.76 (dd, J=3.98, 2.08 Hz, 2H) 4.20 (q, J=7.20 Hz, 4H) 6.19 (s, 1H) 7.06-8.88 (m, 7H).

Workup

  1. customThe flask was sealed
  2. customflushed with nitrogen for three times
  3. temperatureheated at 100° C. for 1 hour
  4. customThe organic solvent was evaporated under vacuum and EtOAc (3×100 ml)
  5. extractionto extract
  6. washthe combined organic solvent was washed by saturated aqueous sodium bicarbonate solution, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (heptanes/acetone 1/2)

Sources & evidence

ORD record
ord-8095dd3c7880400695bf5dbd7180b5d5
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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