2,6-Lutidine → HCID 72191520, compound

HRID 2173908Notes

Reaction equation

HRID 2173908 reaction equation
[F:1][CH:2]([F:24])[O:3][C:4]1[C:5]([CH:21]=CC)=[C:6]2[C:10](=[C:11]([CH3:13])[CH:12]=1)[N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]=[CH:7]2.N1C(C)=CC=CC=1C.[O:33]1CCOCC1>O.C(Cl)Cl.O=[Os](=O)(=O)=O>[F:24][CH:2]([F:1])[O:3][C:4]1[C:5]([CH:21]=[O:33])=[C:6]2[C:10](=[C:11]([CH3:13])[CH:12]=1)[N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH:8]=[CH:7]2

Participants

7

Reactant 3

HCID 79372,6-LutidineHCID 312751,4-DioxaneHCID 86701443HCID 86701443, compound

Product 1

HCID 72191520HCID 72191520, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-(difluoromethoxy)-7-methyl-4-(prop-1-en-1-yl)-1H-indole-1-carboxylate (1.83 g, 5.42 mmol) in dioxane (40 mL) and water (13.56 mL) at 0° C., 2,6-lutidine (1.26 mL, 10.85 mmol), OsO4 (1.36 mL, 0.108 mmol) (2.5% in t-BuOH) and NaIO4 (4.64 g, 21.70 mmol) were added and the reaction was stirred at room temperature. After 1 hour the reaction was diluted with DCM and the layers separated. The organics were washed with sat. NH4Cl and water, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-40% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.45 (s, 1H) 7.93 (d, J=3.54 Hz, 1H) 7.37 (d, J=3.54 Hz, 1H) 7.34 (t, J=73.6 Hz, 1H) 7.16 (s, 1H) 2.63 (s, 3H) 1.61 (s, 9H). MS (ESI+) m/z 326.2 (M+H).

Workup

  1. customthe layers separated
  2. washThe organics were washed with sat. NH4Cl and water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (0-40% EtOAc in heptanes)

Sources & evidence

ORD record
ord-86c101f44a8f4e7d963ec5a736a13252
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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