Triethylamine → 3-Chloro-5-(4-fluoro-3-nitrophenylethynyl)-pyridine

HRID 606943Notes

Reaction equation

HRID 606943 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[CH:9])[CH:7]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].C(N(CC)CC)C>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[C:9][C:14]2[CH:15]=[CH:16][C:11]([F:10])=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 145905821-Fluoro-4-iodo-2-nitrobenzeneHCID 235008873-Chloro-5-ethynylpyridine

Product 1

HCID 670482143-Chloro-5-(4-fluoro-3-nitrophenylethynyl)-pyridineYield 54%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

Add bis(triphenylphosphine)palladium (II) dichloride (150 mg, 0.22 mmol), copper (I) iodide (83 mg, 0.44 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (600 mg, 4.4 mmol) to a solution of 1-fluoro-4-iodo-2-nitrobenzene, (prepared as described in PREPARATION 46), (1.22 g, 4.6 mmol) in triethylamine (6.6 mL, 65.3 mmol). Stir at 60° C. for 18 h then concentrate. Purify by silica gel chromatography, eluting with a gradient of 100:0 to 90:10 dichloromethane:ethyl acetate, followed by a second silica gel chromatography, eluting with 95:5 to 60:40 hexanes:ethyl acetate, to give the title compound as a light yellow solid (650 mg, 54%).

Workup

  1. concentrationthen concentrate
  2. customPurify by silica gel chromatography
  3. washeluting with a gradient of 100:0 to 90:10 dichloromethane
  4. washeluting with 95:5 to 60:40 hexanes

Sources & evidence

ORD record
ord-cdba4cf83cd640fc9dbdae848a9a0ada
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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