Triethylsilane → 3-(4-Fluorophenyl)-5-methylindoline

HRID 717754

반응식

HRID 717754 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[NH:10][CH:9]=2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=3)[NH:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 103763663-(4-fluorophenyl)-5-methyl-1H-indole

생성물 1

HCID 673731403-(4-Fluorophenyl)-5-methylindoline수율 60%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

To the cooled solution of 3-(4-fluorophenyl)-5-methyl-1H-indole (2 g, 0.0088 mol) in TFA (60 mL) was added triethylsilane (6 mL) dropwise at 0° C., and the reaction mixture was stirred for 4 h at RT. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure, the residue treated with saturated sodium bicarbonate solution, and extracted with EtOAc (3×150 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the product purified by column chromatography (10% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a yellow colored oil (1.2 g, 60% yield).

후처리

  1. customAfter completion of reaction (monitored by TLC), solvent
  2. customwas removed under reduced pressure
  3. additionthe residue treated with saturated sodium bicarbonate solution
  4. extractionextracted with EtOAc (3×150 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe product purified by column chromatography (10% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch)

출처 및 근거

ORD 기록
ord-6a85620625e344ddb30294a25af54a7d
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193728B2

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