Tetrabutylammonium Fluoride → HCID 59129336, 화합물

HRID 1403932노트

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HRID 1403932 반응식
[CH3:1][C:2]1([C:5]#[C:6][C:7]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=2[NH:16]C(=O)CCC)[CH2:4][CH2:3]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][C:2]1([C:5]2[NH:16][C:8]3[C:7]([CH:6]=2)=[CH:12][C:11]([N+:13]([O-:15])=[O:14])=[CH:10][CH:9]=3)[CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 59129340N-(2-(1-methyl-cyclopropylethynyl)-4-nitro-phenyl]-butyramide

생성물 1

HCID 59129336HCID 59129336, 화합물수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of N-[2-(1-methyl-cyclopropylethynyl)-4-nitro-phenyl]-butyramide (1.3 g, 4.6 mmol) and TBAF (2.4 g, 9.2 mmol) in THF (20 mL) was heated at reflux for 24 h. The mixture was cooled to room temperature and poured into ice water. The mixture was extracted with CH2Cl2 (30 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1) to afford 2-(1-methylcyclopropyl)-5-nitro-1H-indole (0.70 g, 71%). 1H NMR (400 MHz, CDCl3) δ 8.56 (brs, 1H), 8.44 (d, J=2.0 Hz, 1H), 8.01 (dd, J=2.4, 8.8 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 6.34 (d, J=1.6 Hz, 1H), 1.52 (s, 3H), 1.03-0.97 (m, 2H), 0.89-0.83 (m, 2H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. extractionThe mixture was extracted with CH2Cl2 (30 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=10/1)

출처 및 근거

ORD 기록
ord-bb36c6ea5ded4c45b1a7f2ef63d79858
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912199B2

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