Triethylamine → 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbonitrile

HRID 644017노트

반응식

HRID 644017 반응식
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH:14]1([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[O:30][CH3:31])[C:23]([C:32]([NH2:34])=O)=[CH:22]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C.O1CCOCC1>O>[CH:14]1([CH2:20][N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[O:30][CH3:31])[C:23]([C:32]#[N:34])=[CH:22]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 312751,4-DioxaneHCID 686974651-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid amide

생성물 1

HCID 686987431-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbonitrile수율 64.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Trifluoroacetic anhydride (12.0 g, 57.1 mmol) was added dropwise to a mixture of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carboxylic acid amide (4.1 g, 14.3 mmol), triethylamine (11.6 g, 115 mmol), and 1,4-dioxane (250 ml) under ice-water cooling. The resulting mixture was stirred at room temperature for 12 h. Water (30 ml) was added and the resulting mixture was concentrated in vacuo. Water (300 ml) was added to the obtained residue, and the mixture was extracted with dichloromethane (4×300 ml). The organic layers were combined, washed with 5% aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate, and concentrated in vacuo. The obtained residue was purified by column chromatography eluting with 10% (v/v) ethyl acetate in n-heptane to afford 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbonitrile as a crystalline solid (2.48 g).

후처리

  1. concentrationthe resulting mixture was concentrated in vacuo
  2. additionWater (300 ml) was added to the obtained residue
  3. extractionthe mixture was extracted with dichloromethane (4×300 ml)
  4. washwashed with 5% aqueous sodium hydrogen carbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by column chromatography
  8. washeluting with 10% (v/v) ethyl acetate in n-heptane

출처 및 근거

ORD 기록
ord-ea83d42b1c294693b0f60c08f8f92599
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700634B2

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