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

HRID 913841Notes

Reaction equation

HRID 913841 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-3db3af3199d642f19db7ee281b8957e1
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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