1,2-Diiodoethane → HCID 178434246, compound
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[O:15][CH:14]=[N:13][CH:12]=3)[CH:9]=2)[NH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[I:26]CCI.S([O-])([O-])(=O)=S.[Na+].[Na+]>CCOCC.C1COCC1>[I:26][C:14]1[O:15][C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[CH3:1])=[CH:12][N:13]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a 150 mL round-bottomed flask was added 3-methyl-5-(oxazol-5-yl)-1H-indazole (0.90 g, 4.52 mmol), and THF (20 mL). The resulting reaction mixture was stirred at −78° C. The solution was then treated dropwise via syringe with lithium bis(trimethylsilyl)amide (1.0 M solution in THF (13.6 mL, 13.6 mmol)), and the reaction was stirred for 1 hour at −78° C. A THF solution of 1,2-diiodoethane (5.20 mmol) was then added dropwise and the reaction was allowed to warm to room temperature for 1 hour. The reaction was then poured into a 1:1 mixture of ether and saturated sodium thiosulfate. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 10 to 50% EtOAc in Hexanes to give the desired product as a tan powder (1.01 g, 69% yield). LCMS (API-ES) m/z (%): 325 (100%, M++H).
Workup
- customThe resulting reaction mixture
- stirringthe reaction was stirred for 1 hour at −78° C
- temperatureto warm to room temperature for 1 hour
- customchromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
- washeluting with a gradient of 10 to 50% EtOAc in Hexanes
Sources & evidence
- ORD record
- ord-53f381441d1e43b0b1d6ce2cd2cda013
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897619B2
Reaction notes
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