Water → 2-Bromo-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide

HRID 39510Notes

Reaction equation

HRID 39510 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])=[CH:9][N:10]=1)[C:5](O)=[O:6].C(N1C=CN=C1)([N:22]1C=CN=C1)=O.C([O-])(=O)C.[NH4+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[F:19])=[CH:9][N:10]=1)[C:5]([NH2:22])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 517165Ammonium AcetateHCID 576496492-Bromo-5-[(2-fluoro-4-iodophenyl)amino]isonicotinic acid

Product 1

HCID 117047692-Bromo-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamideYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-[(2-fluoro-4-iodophenyl)amino]isonicotinic acid (145.0 mg, 0.33 mmol) in N,N-dimethylformamide (1.50 ml), 1,1′-carbonylbis(1H-imidazole) (60 mg, 0.36 mmol) was added, and the mixture was stirred at room temperature for 7 hours to obtain a homogeneous solution. Ammonium acetate (65 mg, 0.83 mmol) was added, and stirred for 2 h. Water (10 ml) was added, and the precipitated solid was filtered, washed with hot methanol to obtain 2-Bromo-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide as an yellow solid (85 mg, 58%) LC/MS: [9.59 min; 436, 438]

Workup

  1. customto obtain a homogeneous solution
  2. stirringstirred for 2 h
  3. filtrationthe precipitated solid was filtered
  4. washwashed with hot methanol

Sources & evidence

ORD record
ord-b149f7c73543424883c0dce7a7930514
Source dataset
uspto-grants-2013_09
Patent number
US08524911B2

Reaction notes

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