Pyridine → N-[2-Fluoro-5-(5-methoxypyridin-3-ylethynyl)-phenyl]-methanesulfonamide

HRID 606945Notes

Reaction equation

HRID 606945 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[N:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=2)=[CH:4][C:3]=1[NH2:18].N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:11]=[N:12][CH:13]=[C:14]([O:16][CH3:17])[CH:15]=2)=[CH:4][C:3]=1[NH:18][S:26]([CH3:25])(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67047543HCID 67047543, compound

Product 1

HCID 67047716N-[2-Fluoro-5-(5-methoxypyridin-3-ylethynyl)-phenyl]-methanesulfonamideYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2-fluoro-5-(5-methoxypyridin-3-ylethynyl)-phenylamine, (prepared as described in EXAMPLE 111), (330 mg, 1.36 mmol) in dichloromethane (10 mL) under nitrogen and cool to 0° C. Add pyridine (0.240 ml, 2.99 mmol) followed by methanesulfonyl chloride (0.106 mL, 1.36 mmol) dropwise via syringe. Stir 14 h while allowing to warn to room temperature. Concentrate and purify by silica gel chromatography, eluting with 80:20 ethyl acetate:hexanes to 100% ethyl acetate, to give the title compound as a white solid (250 mg, 57%).

Workup

  1. customto warn to room temperature
  2. concentrationConcentrate
  3. custompurify by silica gel chromatography
  4. washeluting with 80:20 ethyl acetate

Sources & evidence

ORD record
ord-596b2acfb2844e95bcb9080e62814ba7
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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