Triethylsilane → methyl 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylate
Reaction equation
[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:3]=1[C:4]([C:6]1[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[NH:9][CH:10]=1)=O.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:3]=1[CH2:4][C:6]1[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[NH:9][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a TFA 30 mL solution of methyl 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylate in a sealed tube was added triethylsilane (2.55 g, 22 mmol). The resulting reaction mixture was heated in an oil bath at 70° C. overnight. The reaction was concentrated and diluted with isopropylacetate and saturated sodium bicarbonate aqueous solution. The organic layer was separated. The aqueous layer was extracted with isopropylacetate twice. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and chromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes to give the title compound (840 mg).
Workup
- customThe resulting reaction mixture
- concentrationThe reaction was concentrated
- additiondiluted with isopropylacetate and saturated sodium bicarbonate aqueous solution
- customThe organic layer was separated
- extractionThe aqueous layer was extracted with isopropylacetate twice
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customchromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes
Sources & evidence
- ORD record
- ord-d23573c4764441caa5d00332038117bf
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513289B2
Reaction notes
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