1-Isopropylsulfonyl-2-amino-6-iodobenzimidazole → HCID 17981838, compound

HRID 2252071Notes

Reaction equation

HRID 2252071 reaction equation
[CH3:1][C:2]1[S:3][C:4]([Sn](CCCC)(CCCC)CCCC)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH:26]([S:29]([N:32]1[C:36]2[CH:37]=[C:38](I)[CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH2:42])(=[O:31])=[O:30])([CH3:28])[CH3:27]>CN(C)C=O.C(OCC)(=O)C>[CH:26]([S:29]([N:32]1[C:36]2[CH:37]=[C:38]([C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=3[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH2:42])(=[O:30])=[O:31])([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 106425631-Isopropylsulfonyl-2-amino-6-iodobenzimidazoleHCID 17981611HCID 17981611, compound

Product 1

HCID 17981838HCID 17981838, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stir a mixture of 2-methyl-4-phenyl-5-(tributylstannyl)thiazole (0.1 g, 0.21 mmol), 1-isopropylsulfonyl-2-amino-6-iodobenzimidazole (0.07 g, 0.21 mmol), and (acetonitrile)palladium(II) chloride (0.021 mmol) in dry dimethylformamide (2 mL) at 100° C. for 4 hours under a nitrogen atmosphere. Cool to room temperature and dilute with ethyl acetate (20 mL). Wash sequentially with water (3×5 mL) and saturated aqueous sodium chloride (3×5 mL), dry over sodium sulfate, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 7:1 dichloromethane:acetonitrile to provide the title compound as a white solid in 2% yield. MS(ES+): m/z=413.0 (M+H)+

Workup

  1. washWash sequentially with water (3×5 mL) and saturated aqueous sodium chloride (3×5 mL)
  2. dry with materialdry over sodium sulfate
  3. concentrationconcentrate under reduced pressure
  4. washeluting with 7:1 dichloromethane

Sources & evidence

ORD record
ord-7573a41ee85d4d14b61e8b808eef904e
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

Loading…