Triethylsilane → 3-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(2,3-dihydro-1-methyl-1H-indol-5-yl)-2-pyridinamine

HRID 1053122노트

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HRID 1053122 반응식
[CH:1]1([C:4]2[O:8][C:7]([C:9]3[C:10]([NH2:25])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[N:20]([CH3:24])[CH:19]=[CH:18]5)[CH:14]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.O>[CH:1]1([C:4]2[O:8][C:7]([C:9]3[C:10]([NH2:25])=[N:11][CH:12]=[C:13]([C:15]4[CH:16]=[C:17]5[C:21](=[CH:22][CH:23]=4)[N:20]([CH3:24])[CH2:19][CH2:18]5)[CH:14]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 902773103-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-1H-indol-5-yl)-2-pyridinamine

생성물 1

HCID 771059543-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)-5-(2,3-dihydro-1-methyl-1H-indol-5-yl)-2-pyridinamine수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 6422Trifluoroacetic acid용매

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온도
0 °C

실험 절차

To a solution of 3-(5-cyclopropyl-[1,3,4]oxadiazol-2-yl)-5-(1-methyl-1H-indol-5-yl)-pyridin-2-ylamine (160 mg, 0.48 mmol) in TFA at 0° C. was added triethylsilane (0.2 mL, 1.20 mmol) drop-wise over a period of 5 min, and stirred for 2 h at 0° C. The reaction mixture was diluted with water (20 mL) and neutralized with saturated aqueous NaHCO3 solution and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to get crude product. The crude product was purified by column chromatography using 100-200 mesh silica gel and compound was eluted with 40% ethyl acetate in petroleum ether to afford the title compound.

후처리

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto get crude product
  6. customThe crude product was purified by column chromatography
  7. washwas eluted with 40% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-73b31d1a120b469bae9fb0823fd6c88e
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09393248B1

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