Chloride → 1-(2-(3,4,5-Trimethoxyphenylethynyl)pyridin-3-yl)ethanone

HRID 1496858Notes

Reaction equation

HRID 1496858 reaction equation
[C:1]([C:4]1[C:5](Br)=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[C:11]([C:13]1[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=1)#[CH:12].C(N(CC)CC)C.[Cl-]>C1COCC1.C(Cl)Cl>[CH3:24][O:23][C:15]1[CH:14]=[C:13]([C:11]#[C:12][C:5]2[C:4]([C:1](=[O:3])[CH3:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH:18]=[C:17]([O:19][CH3:20])[C:16]=1[O:21][CH3:22]

Participants

7

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 99903691-(2-Bromopyridin-3-yl)ethan-1-oneHCID 118302605-Ethynyl-1,2,3-trimethoxybenzene

Product 1

HCID 712386601-(2-(3,4,5-Trimethoxyphenylethynyl)pyridin-3-yl)ethanoneYield 57.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Step 1 (=Reaction 1): 100 mg 3-Acetyl-2-bromopyridine, 140 mg 5-ethynyl-1,2,3-trimethoxybenzene 2.1, 101 μL triethylamine, 17 mg triphenylphosphinpalladium(II) chlorid, 1 mg Cu(I)I were suspended in 4 mL THF under argon atmosphere and stirred for 1 h at 25° C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and saturated NH4Cl solution. The organic phase was concentrated and the mixture separated via FCC (10 g SiO2, Cyclohexane→cyclohexane/ethylacetate 70:30) to yield 90 mg 1-(2-(3,4,5-trimethoxyphenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=1.21 min (method E) M+H=312.

Workup

  1. customStep 1 (=Reaction 1)
  2. extractionextracted with diluted aq. NH3 and saturated NH4Cl solution
  3. concentrationThe organic phase was concentrated
  4. customthe mixture separated via FCC (10 g SiO2, Cyclohexane→cyclohexane/ethylacetate 70:30)

Sources & evidence

ORD record
ord-dc637962b4f049c5892ca70e5c20a7a8
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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