N-bromobutanimide → HCID 69004041, compound

HRID 2102398Notes

Reaction equation

HRID 2102398 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]2[N:11]([CH3:14])[CH:12]=[N:13][C:8]2=[C:7]([F:15])[C:6]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[F:23])=[O:4].C1C(=O)N([Br:31])C(=O)C1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]2[N:11]([CH3:14])[CH:12]=[N:13][C:8]2=[C:7]([F:15])[C:6]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Br:31])=[CH:19][C:18]=1[F:23])=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 690052127-fluoro-6-(2-fluorophenylamino)-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid methyl ester

Product 1

HCID 69004041HCID 69004041, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-fluoro-6-(2-fluorophenylamino)-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid methyl ester (1.00 equivalent) in DMF is added NBS (1.20 equivalents) at room temperature. After stirring for 16 hours at room temperature, the reaction mixture is diluted with EtOAc and washed with water. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo to give the crude material that is purified by trituration or flash column chromatography to afford the desired product as necessary.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give the crude material that
  6. customis purified by trituration or flash column chromatography

Sources & evidence

ORD record
ord-2aa28bb1d3194141a5b2669176f0bc29
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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