Sodium Iodide → HCID 57931417, compound

HRID 1468565Notes

Reaction equation

HRID 1468565 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[I:11])=O.[C:12]([NH:19][C:20]([NH2:22])=[NH:21])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[I-].[Na+]>CN(C=O)C>[C:15]([O:14][C:12]([N:19]1[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[I:11])=[CH:2][N:21]=[C:20]1[NH2:22])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 13805529HCID 13805529, compoundHCID 178454308HCID 178454308, compound

Product 1

HCID 57931417HCID 57931417, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-1-(2-iodophenyl)ethanone (2.70 g, 8.31 mmol) in anhydrous DMF (27 mL) was added Boc-guanidine (4.00 g, 24.9 mmol) and sodium iodide (2.47 g, 16.6 mmol). The reaction was stirred at ambient temperature for 72 hours upon which the mixture was partitioned between EtOAc (150 mL) and water (75 mL). The organic layer was successively washed with water (3×50 mL) and brine (2×50 mL) before being dried (Na2SO4) and evaporated to dryness. The resulting crude oil was purified via flash column chromatography (10-30% EtOAc/CH2Cl2) to obtain the target 2-amino-5-(2-iodophenyl)imidazole-1-carboxylic acid tert-butyl ester (1.84 g, 58%) as a tan foam: mp=121° C. (dec.); 1H NMR (400 MHz, DMSO-d6) δ 7.92 (m, 1H), 7.27 (dd, 1H, J=1.6, 8.0 Hz), 7.49 (s, 1H), 7.41 (m, 1H), 7.00 (m, 1H), 6.59 (br s, 2H), 1.57 (s, 9H); 13C NMR (100 MHz, DMSO-d6) δ 149.6, 148.8, 140.3, 137.4, 130.1, 128.8, 128.1, 108.6, 95.7, 85.0, 27.5; HRMS (ESI) calcd for C14H17IN3O2 (MH+) 386.0360. found 386.0359.

Workup

  1. customwas partitioned between EtOAc (150 mL) and water (75 mL)
  2. washThe organic layer was successively washed with water (3×50 mL) and brine (2×50 mL)
  3. dry with materialbefore being dried (Na2SO4)
  4. customevaporated to dryness
  5. customThe resulting crude oil was purified via flash column chromatography (10-30% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-4414ce5f33fd46ad8a4df1bcdfa0c81f
Source dataset
uspto-grants-2015_04
Patent number
US09005643B2

Reaction notes

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