Water → 5-chloro-N-((1-(4-iodophenyl)-1H-pyrrol-3-yl)methyl)thiophene-2-carboxamide

HRID 643025Notes

Reaction equation

HRID 643025 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[I:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]2[CH:48]=[CH:47][C:46]([CH2:49][NH2:50])=[CH:45]2)=[CH:40][CH:39]=1.O>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:50][CH2:49][C:46]2[CH:47]=[CH:48][N:44]([C:41]3[CH:42]=[CH:43][C:38]([I:37])=[CH:39][CH:40]=3)[CH:45]=2)=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68507533(1-(4-iodophenyl)-1H-pyrrol-3-yl)methanamine

Product 1

HCID 685028095-chloro-N-((1-(4-iodophenyl)-1H-pyrrol-3-yl)methyl)thiophene-2-carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-thiophene-2-carboxylic acid (60 mg, 0.37 mmol) and TEA (0.102 mL, 0.73 mmol) in DMF (4 mL) was added BOP (196 mg, 0.44 mmol). After 10 min of stirring, the solution was added to a sample of (1-(4-iodophenyl)-1H-pyrrol-3-yl)methanamine (91 mg, 0.31 mmol) in a flask. The mixture was stirred at room temperature overnight. H2O was added to induce precipitation. The resulting precipitate was collected and dried on vacuum to give 5-chloro-N-((1-(4-iodophenyl)-1H-pyrrol-3-yl)methyl)thiophene-2-carboxamide (118 mg).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customprecipitation
  3. customThe resulting precipitate was collected
  4. customdried on vacuum

Sources & evidence

ORD record
ord-120e6cf8bbd044d7a05abdbf9809c015
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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