Cesium carbonate → HCID 90390501, compound

HRID 1479872Notes

Reaction equation

HRID 1479872 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[O:13]1[CH2:14][CH2:15][N:10]([C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:21]3[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=3)[N:3]=2)[CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 830745812-Chloro-6-morpholin-4-yl-isonicotinonitrile

Product 1

HCID 90390501HCID 90390501, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The nitrile 25B (3.2 g, 14.4 mmol), 4-trifluoromethylphenylboronic acid (3.01 g, 1 mol eq), palladium acetate (65 mg, 0.02 mol eq), cesium carbonate (9.38 g, 2 mol eq), and XPhos (265 mg, 0.04 mol eq) were mixed, placed under a nitrogen atmosphere and dioxane (12 mL) was added. The mixture was heated at 100° C. overnight. After cooling, the mixture was filtered through a celite pad, washed with dioxane (2×30 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (7/3 Petroleum ether/EtOAc) to afford 26B as yellow solid (1.33 g, 40% Yield). 1HNMR (DMSO, 400 MHz) δ 3.63 (m, 4H, J=1.9), 3.74 (m, 4H, J=2), 7.38 (s, 1H), 7.74 (s, 1H), 7.84 (d, 2H, J=8.1), 8.32 (d, 2H, J=8).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through a celite pad
  3. washwashed with dioxane (2×30 mL)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (7/3 Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-c0695b072a034e42b471519c8320ef1a
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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