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Triethylamine → 8-Chloro-1-(2-fluoro-4-iodophenyl)-5-methyl-3,5-dihydrodiimidazo[4,5-b:4',5'-e]pyridin-2(1H)-one

HRID 558217
Notes
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Reaction equation

HRID 558217 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[C:6](C(O)=O)[N:5]=[C:4]2[N:20]([CH3:23])[CH:21]=[N:22][C:3]=12.C([N:26]([CH2:29]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[N:22]=[CH:21][N:20]([CH3:23])[C:4]=2[N:5]=[C:6]2[NH:26][C:29](=[O:38])[N:8]([C:9]3[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=3[F:16])[C:7]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 595194827-chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid

Product 1

HCID 595194258-Chloro-1-(2-fluoro-4-iodophenyl)-5-methyl-3,5-dihydrodiimidazo[4,5-b:4',5'-e]pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a suspension of 7-chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (2.75 g, 6.16 mmol) in toluene (80 ml) is added triethylamine (2.57 ml, 18.5 mmol) and diphenylphosphoryl azide (1.56 ml, 7.7 mmol). The reaction is heated at reflux for 4 h. The mixture is cooled to room temperature and concentrated to dryness. Silica gel chromatography yields the title compound.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 4 h
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-434bf7bb43a949779de381a89f978ab1
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063049B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes