1H-imidazole-2-carbaldehyde → 2-(2-formyl-1H-imidazol-1-yl)-N-(3-iodophenyl)acetamide

HRID 1484607Notes

Reaction equation

HRID 1484607 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([I:12])[CH:7]=1)=[O:4].[NH:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH:18]=[O:19].CCN(C(C)C)C(C)C>CN(C=O)C>[CH:18]([C:14]1[N:13]([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([I:12])[CH:7]=2)=[O:4])[CH:17]=[CH:16][N:15]=1)=[O:19]

Participants

5

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 81531DiisopropylethylamineHCID 448834702-bromo-N-(3-iodophenyl)acetamide

Product 1

HCID 866927222-(2-formyl-1H-imidazol-1-yl)-N-(3-iodophenyl)acetamideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-N-(3-iodophenyl)acetamide (2.67 g, 7.83 mmol), 1H-imidazole-2-carbaldehyde (0.752 g, 7.83 mmol) and DIPEA (10 mL) in DMF (20 mL) was stirred at 80° C. for 4 hrs. The solvent was evaporated under reduced pressure to afford a residue, which was purified by Biotage eluting with DCM in hexanes to 10% MeOH in DCM to give 2-(2-formyl-1H-imidazol-1-yl)-N-(3-iodophenyl)acetamide (2.60 g, 94%). 1H NMR (400 MHz, DMSO) 9.64 (s, 1H), 8.17 (brs, 1H), 8.04 (s, 1H), 7.60 (s, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.28 (s, 1H), 7.10 (t, J=8.0 Hz, 1H), 5.23 (s, 2H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto afford a residue, which
  3. customwas purified by Biotage
  4. washeluting with DCM in hexanes to 10% MeOH in DCM

Sources & evidence

ORD record
ord-8dd05e96cb254a9c94f589c4062202ac
Source dataset
uspto-grants-2016_08
Patent number
US09422251B2

Reaction notes

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