Triethylamine → 5-Nitro-3-(trimethylsilylethynyl)-indazole-1 carboxylic acid tert-butyl ester

HRID 1823916노트

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HRID 1823916 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10](Br)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][Si:29]([C:32]#[CH:33])([CH3:31])[CH3:30]>CN(C=O)C.[Cu](I)I>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([C:33]#[C:32][Si:29]([CH3:31])([CH3:30])[CH3:28])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 8471Triethylamine2회HCID 66111TrimethylsilylacetyleneHCID 222608361-Boc-3-bromo-5-nitro-1H-indazole

생성물 1

HCID 600647035-Nitro-3-(trimethylsilylethynyl)-indazole-1 carboxylic acid tert-butyl ester수율 45.1%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

3-Bromo 5-nitro-indazole-1-carboxylic acid tert-butyl ester (2 g, 5.8 mmol) was dissolved in dry DMF (30 mL) under nitrogen and triethylamine (1.6 mL, 1.6 mmol) added. Copper iodide (20 mg, 0.12 mmol), trimethylsilylacetylene (2.5 mL, 17.4 mmol) palladium bis-triphenylphosphine dichloride (84 mg, 0.12 mmol) and a further 1.6 mL of triethylamine were added and the mixture heated at 50° C. overnight. The reaction mixture was allowed to cool to room temperature and concentrated. The residue was taken up in EtOAc and filtered through a plug of Celite®. The filtrate was washed with saturated ammonium chloride solution and dried over sodium sulfate then concentrated to a black foam. Purification by chromatography (silica, 1:1 petrol-EtOAc) gave the title compound as a black solid (940 mg, 45%); MS (ES+) m/e=360.

후처리

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. filtrationfiltered through a plug of Celite®
  4. washThe filtrate was washed with saturated ammonium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationthen concentrated to a black foam
  7. customPurification by chromatography (silica, 1:1 petrol-EtOAc)

출처 및 근거

ORD 기록
ord-55b7a0b7624949af99d16aead348262a
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041687B2

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