Cesium carbonate → HCID 66832355, compound

HRID 1914527

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:9]=1)[C:5]#[N:6].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.O1CCOCC1>[N:10]1([C:8]2[CH:7]=[C:4]([CH:3]=[C:2]([C:20]3[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=3)[N:9]=2)[C:5]#[N:6])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-6-pyrrolidin-1-yl-isonicotinonitrile (0.18 g, 0.87 mmol), 4-trifluoromethylphenylboronic acid (0.18 g, 0.95 mmol), palladium acetate (3.9 mg, 0.02 mmol), cesium carbonate (0.56 g, 1.73 mmol), and XPhos (17 mg, 0.04 mmol) were combined, placed under a nitrogen atmosphere and dioxane (1.0 mL) was added. The reaction vessel was sealed and heated to 100° C. for 2 hours. The reaction mixture was cooled to rt, filtered through celite, concentrated under reduced pressure and purified by flash column chromatography (0%-80% EtOAc in hexane) to provide the desired product (253 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 8.11 (d, J=8.1 Hz, 2H), 7.70 (d, J=8.2 Hz, 2H), 7.15 (d, J=0.8 Hz, 1H), 6.54 (d, J=0.9 Hz, 1H), 3.55 (bs, 4H), 2.13-1.99 (m, 4H).

Workup

customThe reaction vessel was sealed
temperatureThe reaction mixture was cooled to rt
filtrationfiltered through celite
concentrationconcentrated under reduced pressure
custompurified by flash column chromatography (0%-80% EtOAc in hexane)

Sources & evidence

ORD record: ord-6a7a22c1c5774919996decbdd2dafcfb
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614201B2

Linked notes

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