4-Bromo-1-fluoro-2-nitrobenzene → HCID 67047850, compound

HRID 606895Notes

Reaction equation

HRID 606895 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)#[CH:2].Br[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([N+:19]([O-:21])=[O:20])[CH:13]=1>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>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:2]#[C:1][C:3]2[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=2)=[CH:13][C:14]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 2

HCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 210973493-Ethynyl-5-methoxypyridine2×

Product 1

HCID 67047850HCID 67047850, compoundYield 43.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Sequentially add 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (400 mg, 3.0 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.100 g, 0.14 mmol) and copper (I) iodide (53 mg, 0.28 mmol) to a solution of 4-bromo-1-fluoro-2-nitrobenzene (616 mg, 2.8 mmol) in triethyl amine (6 mL) and heat for 2 h at 60° C. Add additional 3-ethynyl-5-methoxypyridine (100 mg, 0.75 mmol) and continue heating for 1 h. Concentrate and purify the residue by silica gel chromatography, eluting with 30:70 to 40:60 ethyl acetate:hexanes, to give the title compound as a pale yellow solid (330 mg, 43%).

Workup

  1. temperaturecontinue heating for 1 h
  2. concentrationConcentrate
  3. custompurify the residue by silica gel chromatography
  4. washeluting with 30:70 to 40:60 ethyl acetate

Sources & evidence

ORD record
ord-362a7ccba1e14968a6c0f27c550c8695
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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