Cesium carbonate → HCID 125505052, compound

HRID 1479866Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([N:10]([CH3:12])[CH3:11])[N:3]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=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>[CH3:11][N:10]([C:4]1[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:25])([F:24])[F:13])=[CH:16][CH:17]=2)[N:3]=1)[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

The nitrile 25C (2.0 g, 11.1 mmol), 4-trifluoromethylphenylboronic acid (2.32 g, 1.1 mol eq), palladium acetate (50 mg, 0.02 mol eq), cesium carbonate (7.23 g, 2 mol eq), and XPhos (210 mg, 0.04 mol eq) were mixed, placed under a nitrogen atmosphere and dioxane (10 mL) was added. The mixture was heated at 100° C. for 3 h. After cooling, the mixture was filtered through a celite pad, washed with dioxane (2×20 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (9.5/0.5 petroleum ether/EtOAc) to afford 26E as a pale yellow solid (2.2 g, 68% Yield). 1HNMR (DMSO, 200 MHz) δ 3.13 (s, 6H), 7.12 (s, 1H), 7.58 (s, 1H), 7.82 (d, 2H, J=7.7), 8.30 (d, 2H, J=7.8).

Workup

temperatureAfter cooling
filtrationthe mixture was filtered through a celite pad
washwashed with dioxane (2×20 mL)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (9.5/0.5 petroleum ether/EtOAc)

Sources & evidence

ORD record: ord-ac569078074d4dd8b199d534dd26fe36
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

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