Triethylamine → 2-Fluoro-5-(5-methoxypyridin-3-ylethynyl)-benzamide

HRID 606933Notes

Reaction equation

HRID 606933 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1)#[CH:2].[F:11][C:12]1[CH:20]=[CH:19][C:18](I)=[CH:17][C:13]=1[C:14]([NH2:16])=[O:15].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:11][C:12]1[CH:20]=[CH:19][C:18]([C:2]#[C:1][C:3]2[CH:4]=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=2)=[CH:17][C:13]=1[C:14]([NH2:16])=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 210973493-Ethynyl-5-methoxypyridineHCID 670478112-Fluoro-5-iodobenzamide

Product 1

HCID 670483412-Fluoro-5-(5-methoxypyridin-3-ylethynyl)-benzamideYield 88.8%

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 (70 mg, 0.10 mmol), copper (I) iodide (38 mg, 0.20 mmol), and 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (350 mg, 2.6 mmol) to a solution of 2-fluoro-5-iodobenzamide, (prepared as described in PREPARATION 44), (0.54 g, 2.0 mmol) in triethylamine (3.1 mL, 30.3 mmol) and heat at 60° C. for 18 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 100:0 to 0:100 dichloromethane:ethyl acetate, to give the title compound as a white solid (480 mg, 68%).

Workup

  1. temperatureCool to room temperature
  2. concentrationconcentrate
  3. customPurify by silica gel chromatography
  4. washeluting with 100:0 to 0:100 dichloromethane

Sources & evidence

ORD record
ord-c8e8b80d793b4bb1b4804ab11c1a8330
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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