Cesium carbonate → HCID 25181924, compound

HRID 1895987Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[N:3]=1.Br[C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].C(C1C=CC=C(C(C)C)C=1[N+]1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C=1)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:18]3[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=3)[CH2:15][CH2:16]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of the compound of Example 3 (0.102 g, 0.48 mmol), 5-bromo-2-cyanopyridine (0.073 g, 0.40 mmol), cesium carbonate (0.658 g, 2 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (8.8 mg, 0.05 mmol), palladium(II)acetate (0.0046 mg, 0.05 mmol), in anhydrous and degassed THF (3 mL) was heated in a microwave oven at 110° C. for 15 min in a sealed vessel. The reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether 1:1) affording the title product (0.013 g).

Workup

customin anhydrous and degassed THF (3 mL)
temperatureThe reaction mixture was cooled
additionpoured into water
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
customdried on Na2SO4
customevaporated to dryness in vacuo
customto afford a residue, which
customwas purified by flash chromatography (EtOAc—Petroleum Ether 1:1)

Sources & evidence

ORD record: ord-f10bc29da49e4dea94837f08aaa928d6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518916B2

Reaction notes

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