Bromobenzene → 2-Methyl-6-[3-(1-phenylpiperidin-4-ylidene)prop-1-ynyl]pyridine

HRID 1895965

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:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[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:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)[N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of the compound of Example 3 (0.22 g, 1.04 mmol), bromobenzene (0.17 g, 1.04 mmol), cesium carbonate (0.68 g, 2.1 mmol), BINAP (0.031 g, 0.05 mmol), palladium(II)acetate (0.01 mg, 0.05 mmol), in anhydrous and degassed toluene (10 mL) was heated at 110° C. under a nitrogen atmosphere for 12 h 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 2:8) affording the title product (0.30 g).

Workup

customin anhydrous and degassed toluene (10 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 2:8)

Sources & evidence

ORD record: ord-25430e53cc9c41d1a5f6276ae8efe333
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518916B2

Linked notes

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