Cesium carbonate → HCID 87550603, compound

HRID 1895988Notes

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]=[N:20][CH:21]=[CH:22][C:23]=1[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[CH3:24])[CH2:15][CH2:16]2)[N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of the compound of Example 3 (0.102 g, 0.48 mmol), 3-bromo-4-methylpyridine (0.046 g, 0.40 mmol), cesium carbonate (0.658 g, 2 mmol), 2-(dicyclohexylphosphino)biphenyl (8.8 mg, 0.024 mmol), palladium(II)acetate (0.0027 mg, 0.012 mmol), in anhydrous and degassed toluene (3 mL) was heated in a microwave oven at at 150° 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 (CHCl3-1.4 N MeOH NH3 100:0.25) affording the title product (0.008 g).

Workup

customin anhydrous and degassed toluene (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 (CHCl3-1.4 N MeOH NH3 100:0.25)

Sources & evidence

ORD record: ord-a33a5ce789494f87bb75745aea6186af
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518916B2

Reaction notes

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