Ethyl Acetate → {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile

HRID 552309ノート

反応式

HRID 552309 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([N:10]2[C:14]3=[N:15][C:16]([CH3:27])=[CH:17][C:18](OS(C(F)(F)F)(=O)=O)=[C:13]3[C:12]([CH3:28])=[CH:11]2)=[C:5]([CH3:29])[CH:4]=1.C(N(CC)C(C)C)(C)C.[NH:39]1[CH2:44][CH2:43][CH:42]([CH2:45][C:46]#[N:47])[CH2:41][CH2:40]1.C(OCC)(=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:29])[C:6]([N:10]2[C:14]3=[N:15][C:16]([CH3:27])=[CH:17][C:18]([N:39]4[CH2:44][CH2:43][CH:42]([CH2:45][C:46]#[N:47])[CH2:41][CH2:40]4)=[C:13]3[C:12]([CH3:28])=[CH:11]2)=[C:7]([CH3:9])[CH:8]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 100119032-(Piperidin-4-yl)acetonitrileHCID 59843342trifluoromethanesulfonic acid 1-(4-methoxy-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl ester

生成物 1

HCID 67103732{1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile収率 56.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

A mixture of crude trifluoromethanesulfonic acid 1-(4-methoxy-2,6-dimethylphenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl ester (1.1 g), N,N-diisopropylethylamine (0.65 g) and piperidin-4-yl-acetonitrile (1.6 g) was heated at 150° C. in a sealed tube for 7 hours. After cooling to room temperature, ethyl acetate and water were poured into the mixture, and separated. The aqueous phase was extracted with ethyl acetate, and the organic phase was dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1) to obtain {1-[1-(4-methoxy-2,6-dimethyl-phenyl)-3,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-yl]-piperidin-4-yl}-acetonitrile (0.58 g) as a pale yellow crystal.

後処理

  1. temperatureAfter cooling to room temperature
  2. customseparated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified with column chromatography (silica gel: Wako gel C200, eluent: hexane:ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-9166ac52266942a89c3c49465df2f8de
出典データセット
uspto-grants-2011_05
特許番号
US07951811B2

反応ノート

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