Triethylsilane → methyl 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylate

HRID 1894711노트

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HRID 1894711 반응식
[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]=1

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 66646907methyl 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylate

생성물 1

HCID 66646695methyl 4-(2,4,6-trifluorobenzyl)-1H-pyrrole-2-carboxylate

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
70 °C

실험 절차

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).

후처리

  1. customThe resulting reaction mixture
  2. concentrationThe reaction was concentrated
  3. additiondiluted with isopropylacetate and saturated sodium bicarbonate aqueous solution
  4. customThe organic layer was separated
  5. extractionThe aqueous layer was extracted with isopropylacetate twice
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed on silica gel eluting with a gradient solvent mixture of AcOEt and hexanes

출처 및 근거

ORD 기록
ord-d23573c4764441caa5d00332038117bf
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513289B2

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