Imidazole → tert-butyl-[2-(1H-pyrrolo[2,3-b]pyridin-5-yl)propan-2-yloxy]silane
Reaction equation
N1C2=N[CH:7]=[C:8]([CH2:10]O)[CH:9]=[C:4]2[CH:3]=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])(C)C.N1[CH:24]=[CH:23][N:22]=C1.C[N:26]([CH3:29])[CH:27]=O.C(=O)(O)[O-:31].[Na+]>>[C:15]([SiH2:12][O:31][C:8]([CH3:10])([CH3:7])[C:9]1[CH:4]=[C:3]2[CH:24]=[CH:23][NH:22][C:29]2=[N:26][CH:27]=1)([CH3:18])([CH3:17])[CH3:16]Participants
Procedure
Into a 1-neck round-bottom flask was dissolved (1H-pyrrolo[2,3-b]pyridin-5-yl)-methanol (0.506 g, 0.00342 mol; Adesis) and tert-butyldimethylsilyl chloride (575 mg, 0.00381 mol; Aldrich) and 1H-imidazole (355 mg, 0.00521 mol; Fluka) in N,N-dimethylformamide (2.0E1 mL, 0.25 mol; Acros). The reaction was stirred at room temperature overnight. The reaction was diluted with saturated sodium bicarbonate, extracted with ethyl acetate, washed with saturated sodium chloride. The aqueous layers were then extracted with methylene chloride. All organic layers were combined and dried with magnesium sulfate, filtered and evaporated. The residue was taken up in methylene chloride and purified by silica gel chromatography using hexanes/ethyl acetate as eluent (Rf=0.52 in 1:1 hexanes/ethyl acetate) to yield the product in 478 mg yield (53%). MS m/z=263.17 M+H.
Workup
- extractionextracted with ethyl acetate
- washwashed with saturated sodium chloride
- extractionThe aqueous layers were then extracted with methylene chloride
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- customevaporated
- custompurified by silica gel chromatography
- customto yield the product in 478 mg
- customyield (53%)
Sources & evidence
- ORD record
- ord-510b0f0d2bc64fbda2f7b85f6986d3a4
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778977B2
Reaction notes
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