Dimethylformamide → 6-(4-Fluorophenyl)-5-iodo-imidazo[2,1-b]oxazole

HRID 1711773Notes

Reaction equation

HRID 1711773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([CH:15]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.C1C(=O)N([I:23])C(=O)C1.CN(C=O)C>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[I:23])[CH:13]=[CH:12][O:11]3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 574336106-(4-Fluorophenyl)-imidazo[2,1-b]oxazole

Product 1

HCID 594578256-(4-Fluorophenyl)-5-iodo-imidazo[2,1-b]oxazoleYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-(4-fluorophenyl)imidazo[2,1-b]oxazole (4.92 g, 24.3 mmol; prepared according to WO2004110990A2, Example 1, Steps 1-3), NIS (5.75 g, 25.6 mmol), and DMF (100 mL) was stirred at ambient temperature. After about 3 h, the reaction was poured into water (300 mL) and the resulting precipitate was filtered, washing with additional water, and dried in a vacuum oven at about 55-65° C. to give the title compound (7.21 g, 89%): LC/MS (Table 1, Method b) Rt, =2.09 min; MS m/z: 329.1 (M+H)+.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashing with additional water
  3. customdried in a vacuum oven at about 55-65° C.

Sources & evidence

ORD record
ord-c2ac5ffe35dc49e680c8cdaa87ffceb5
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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