Triethylamine → HCID 90040616, compound

HRID 2207328Notes

Reaction equation

HRID 2207328 reaction equation
Br[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 136603Benzene, 1-bromo-4-ethynyl-HCID 223295224-Bromopyridine-3-carbonitrile

Product 1

HCID 90040616HCID 90040616, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-nicotinonitrile (1.10 g, 6.00 mmol) in DMF (20 ml) are added bis(triphenylphosphine)-palladium(II)-chloride (211 mg, 0.30 mmol), copper(I) iodide (34 mg, 0.18 mmol), triethylamine (1.66 ml, 12.0 mmol) and 1-bromo-4-ethynyl-benzene (1.19 g, 6.6 mmol). The mixture is flushed with nitrogen, heated to 80° C. and stirred in a closed reaction vial at this temperature for 4 hours. The reaction mixture is allowed to cool to room temperature and partitioned between water and dichloromethane. The organic phase is washed with 1 N HCl, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 4-(4-bromo-phenylethynyl)-nicotinonitrile as light yellow powder; HPLC/MS 2.09 min (B), [M+H] 283/285.

Workup

  1. customThe mixture is flushed with nitrogen
  2. temperatureto cool to room temperature
  3. custompartitioned between water and dichloromethane
  4. washThe organic phase is washed with 1 N HCl
  5. dry with materialdried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-2020f97080b94e779e524eb42ab1a4a9
Source dataset
uspto-grants-2016_06
Patent number
US09376433B2

Reaction notes

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