Acetic Anhydride → N-[5-(5-Chloropyridin-3-ylethynyl)-2-fluorophenyl]-acetamide

HRID 606947Notes

Reaction equation

HRID 606947 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[CH:10]=[C:11]([C:15]#[C:16][C:17]2[CH:18]=[CH:19][C:20]([F:24])=[C:21]([NH2:23])[CH:22]=2)[CH:12]=[N:13][CH:14]=1>N1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([C:15]#[C:16][C:17]2[CH:18]=[CH:19][C:20]([F:24])=[C:21]([NH:23][C:5](=[O:7])[CH3:6])[CH:22]=2)[CH:12]=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 670475245-(5-Chloropyridin-3-ylethynyl)-2-fluorophenylamine

Product 1

HCID 67048115N-[5-(5-Chloropyridin-3-ylethynyl)-2-fluorophenyl]-acetamideYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add acetic anhydride (113 mg, 1.11 mmol) to a solution of 5-(5-chloropyridin-3-ylethynyl)-2-fluorophenylamine, (prepared as described in EXAMPLE 190) (0.275 g, 1.11 mmol) in pyridine (4 mL). Stir the mixture at room temperature under nitrogen for 18 h then concentrate. Purify by silica gel chromatography, eluting with a gradient of 75:25 to 50:50 with hexanes:ethyl acetate, followed by a second silica gel chromatography, eluting with 75:25 to 60:40 hexanes:ethyl acetate, to give the title compound as a white solid (240 mg, 75%).

Workup

  1. concentrationthen concentrate
  2. customPurify by silica gel chromatography
  3. washeluting with a gradient of 75:25 to 50:50 with hexanes
  4. washeluting with 75:25 to 60:40 hexanes

Sources & evidence

ORD record
ord-05e52521de73499697351accedf92c96
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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