Ethyl Acetate → 5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-7-carbaldehyde

HRID 913841노트

반응식

HRID 913841 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11][OH: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.C[N+]1([O-])CCOCC1.CCOC(C)=O>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[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

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 82029Methyl morpholine oxideHCID 57546160(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol

생성물 1

HCID 575460835-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-7-carbaldehyde

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

To a suspension of (5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol (675 mg, 1.889 mmol), 4-methylmorpholine 4-oxide (443 mg, 3.78 mmol), and molecular sieves (337 mg, 1.889 mmol) in dichloromethane (10 mL) at room temperature was added tetrapropylammonium perruthenate (19.9 mg, 0.057 mmol). After 1.5 h, the crude reaction mixture was loaded directly onto a pre-conditioned column of silica gel (silica gel/dichloromethane). The solvent was then switched directly to 12% EtOAc/Hex and the column run in that solvent system to give 565 mg (84%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 10.31 (s, 1H), 8.11 (d, J=1.8, 1H), 8.05 (s, 1H), 8.03 (d, J=1.8, 1H), 6.04 (s, 2H), 3.45 (m, 2H), 0.81 (m, 2H), −0.12 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 188.9, 135.4, 135.0, 134.2, 130.0, 129.3, 123.0, 114.0, 81.2, 66.4, 17.8, −1.4.

후처리

  1. customthe crude reaction mixture
  2. customto give 565 mg (84%) as a colorless oil

출처 및 근거

ORD 기록
ord-3db3af3199d642f19db7ee281b8957e1
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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