Cesium carbonate → HCID 90390339, compound

HRID 1479875Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([O:10][CH:11]([CH3:13])[CH3:12])[N:3]=1.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=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>[CH:11]([O:10][C:4]1[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:15]([F:26])([F:25])[F:14])=[CH:17][CH:18]=2)[N:3]=1)([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

The nitrile 25H (1.25 g, 6.4 mmol), 4-trifluoromethylphenylboronic acid (1.34 g, 1 mol eq), palladium acetate (29 mg, 0.02 mol eq), cesium carbonate (4.16 g, 2 mol eq), and XPhos (137 mg, 0.04 mol eq) were mixed, placed under a nitrogen atmosphere and dioxane (8 mL) was added. The mixture was heated at 100° C. for 4 h. 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 (9.5/0.5 Petroleum ether/EtOAc) to afford 26M as yellow solid (0.65 g, 36% Yield). 1HNMR (DMSO, 200 MHz) δ 1.37 (d, 6H, J=3.9), 5.15 (m, 1H), 6.7 (s, 1H), 7.32 (s, 1H), 7.87 (d, 2H, J=7.8), 8.33 (d, 2H, J=8).

Workup

temperatureAfter cooling
filtrationthe mixture was filtered through a celite pad
washwashed with dioxane (2×30 mL)
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (9.5/0.5 Petroleum ether/EtOAc)

Sources & evidence

ORD record: ord-523592b1585645c1b3b6cdce957fee6b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

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