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

HRID 1053122ノート

反応式

HRID 1053122 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-73b31d1a120b469bae9fb0823fd6c88e
出典データセット
uspto-grants-2016_07
特許番号
US09393248B1

反応ノート

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