tert-Butyl 4-allyl-5-methoxy-7-methyl-1H-indole-1-carboxylate → tert-Butyl 5-methoxy-7-methyl-4-(prop-1-en-1-yl)-1H-indole-1-carboxylate

HRID 2173929Notes

Reaction equation

HRID 2173929 reaction equation
[CH2:1]([C:4]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:2]=[CH2:3]>C(O)(C(F)(F)F)C(F)(F)F.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:14][O:13][C:12]1[C:4]([CH:1]=[CH:2][CH3:3])=[C:5]2[C:9](=[C:10]([CH3:15])[CH:11]=1)[N:8]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 86701480tert-Butyl 4-allyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

Product 1

HCID 86701481tert-Butyl 5-methoxy-7-methyl-4-(prop-1-en-1-yl)-1H-indole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

To a solution of tert-Butyl 4-allyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (9.8 g, 32.5 mmol) in 1,1,1,3,3,3-hexafluoro-propanol (HFIPA) (40.6 mL) was added to palladium(II) acetate (0.073 g, 0.325 mmol) in 4 mL of HFIPA. The reaction was stirred at room temperature for 4 hours. The reaction was concentrated and absorbed onto silica and then purified by silica gel flash chromatography (0-30% ethyl acetate/heptanes) to provide the title compound. MS (ESI+) m/z 302.25 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. customabsorbed onto silica
  3. custompurified by silica gel flash chromatography (0-30% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-7439ccdba9c04a1fa260ab10107e679b
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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