Sodium periodate → HCID 86644952, compound

HRID 1875185Notes

Reaction equation

HRID 1875185 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([CH:25]=C)[CH:22]=[C:21]([C:27]#[N:28])[CH:20]=2)[C:12]=1[F:29])=[O:8].I([O-])(=O)(=O)=[O:39].[Na+]>C1COCC1.O.CCOC(C)=O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:35])[CH3:36])[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([CH:25]=[O:39])[CH:22]=[C:21]([C:27]#[N:28])[CH:20]=2)[C:12]=1[F:29])=[O:8]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 684870564-chloro-N-({4-chloro-3-[(3-cyano-5-ethenylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

Product 1

HCID 86644952HCID 86644952, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-N-({4-chloro-3-[(3-cyano-5-ethenylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (1.12 g, 1.995 mmol) and sodium periodate (1.280 g, 5.98 mmol) in THF (20 ml) and Water (10 ml) was added osmium tetroxide (2.5 wt % 2-butanol) (0.501 ml, 0.040 mmol) and the reaction mixture was stirred at rt for 5 hours. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-({4-chloro-3-[(3-cyano-5-formylphenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (930 mg, 1.650 mmol, 83% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 9.94 (s, 1H), 8.71 (d, 1H), 8.00 (s, 1H), 7.90 (s, 1H), 7.61 (d, 1H), 7.34-7.47 (m, 2H), 5.59 (s, 2H), 4.47-4.70 (m, 2H), 3.50 (t, 2H), 0.83 (t, 2H), −0.05 (s, 9H).

Workup

  1. washwashed with water
  2. customThe solvent was removed
  3. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-7038d8a7fd1542fe8dff0e8c5cab71dc
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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