5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-7-carbaldehyde → (+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethanol

HRID 913842노트

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HRID 913842 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]=[O:12])[CH:10]=1)[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:6]=[CH:5]2.[CH3:21][Mg]Br>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([OH:12])[CH3:21])[CH:10]=1)[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:6]=[CH:5]2

참가 물질

4

반응물 2

HCID 575460835-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-7-carbaldehydeHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 57546085(+/-)-1-(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)ethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-7-carbaldehyde (600 mg, 1.689 mmol) in tetrahydrofuran (10 mL) at −78° C. was added methylmagnesiumbromide (3M in diethyl ether, 1.13 mL, 3.38 mmol). After 5 min, the ice bath was removed and stirring continued for 30 min. The reaction was cooled to 0° C. and quenched by the cautious addition of saturated ammonium chloride. The mixture was poured into diethyl ether, washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%→25% EtOAc/Hex) gave 575 mg (92%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.89 (s, 1H), 7.76 (s, 1H), 7.61 (s, 1H), 5.92 (d, J=11.6, 1H), 5.80 (d, J=11.6, 1H), 5.56 (m, 1H), 3.46 (m, 2H), 3.26 (s, 1H), 1.64 (d, J=6.4, 3H), 0.80 (m, 2H), −0.11 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 136.2, 133.5, 130.8, 128.1, 126.9, 122.9, 114.8, 80.3, 66.5, 64.6, 23.0, 17.8, −1.4.

후처리

  1. customthe ice bath was removed
  2. waitcontinued for 30 min
  3. customquenched by the cautious addition of saturated ammonium chloride
  4. additionThe mixture was poured into diethyl ether
  5. washwashed with water (2×)
  6. dry with materialbrine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. customColumn chromatography (12%→25% EtOAc/Hex) gave 575 mg (92%) as a colorless oil

출처 및 근거

ORD 기록
ord-118fac5e9227461498b6e3bdc2ffe57a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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