1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl 2-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-2-diazoacetate

HRID 913918노트

반응식

HRID 913918 반응식
[Cl:1][C:2]1[CH:10]=[C:9]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:8]2[C:4](=[CH:5][N:6]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[N:7]=2)[CH:3]=1.C(NC1C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1)(=O)C.N12CCCN=C1CCCCC2>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([C:11](=[N+:37]=[N-:38])[C:12]([O:14][CH3:15])=[O:13])[C:8]2[C:4](=[CH:5][N:6]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[N:7]=2)[CH:3]=1

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 51291854-Acetamidobenzenesulfonyl azideHCID 57545943Methyl 2-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)acetate

생성물 1

HCID 76561042Methyl 2-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)-2-diazoacetate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of methyl 2-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)acetate (1.95 g, 5.49 mmol) and 4-acetamidobenzenesulfonyl azide (1.52 g, 6.32 mmol) in acetonitrile (11 mL) at 0° C. was added 1,8-Diazabicyclo[5.4.0]undec-7-ene (1.04 mL, 6.87 mmol) dropwise over 20 min. The ice bath was removed and stirring continued at room temperature for 1 h. The reaction was partitioned between water and ethyl acetate. The organics were washed with saturated sodium bicarbonate, dried over sodium sulfate, and concentrated. The resulting residue was purified by column chromatography (8%→25% ethyl acetate/n-hexane) to give 1.39 g (66%) as a yellow oil. 1H-NMR (CDC13, 500 MHz) δ 8.01 (s, 1H), 7.79 (d, J=1.5 Hz, 1H), 7.45 (d, J=1.8 Hz, 1H), 5.64 (s, 2H), 3.89 (s, 3H), 3.64 (t, J=8.2 Hz, 2H), 0.93 (t, J=8.4 Hz, 2H), −0.03 (s,9H; 13C NMR (126 MHz, CDCl3) δ ppm 165.9, 143.2, 128.7, 125.3, 123.1, 122.7, 122.5, 116.5, 116.4, 81.8, 67.9, 52.1, 17.8, −1.4.

후처리

  1. customThe ice bath was removed
  2. customThe reaction was partitioned between water and ethyl acetate
  3. washThe organics were washed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography (8%→25% ethyl acetate/n-hexane)
  7. customto give 1.39 g (66%) as a yellow oil

출처 및 근거

ORD 기록
ord-23c154ffd6f545e5a543a1bb2adafe6e
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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