HCID 86701442, compound → HCID 86701443, compound

HRID 2173907Notes

Reaction equation

HRID 2173907 reaction equation
[CH2:1]([C:4]1[C:12]([O:13][CH:14]([F:16])[F:15])=[CH:11][C:10]([CH3:17])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:2]=[CH2:3]>C(O)(C(F)(F)F)C(F)(F)F.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:16][CH:14]([F:15])[O:13][C:12]1[C:4]([CH:1]=[CH:2][CH3:3])=[C:5]2[C:9](=[C:10]([CH3:17])[CH:11]=1)[N:8]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 86701442HCID 86701442, compound

Product 1

HCID 86701443HCID 86701443, compound

Reagents, catalysts & solvents 2

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

Procedure

To solution of tert-butyl 4-allyl-5-(difluoromethoxy)-7-methyl-1H-indole-1-carboxylate (2.05 g, 6.08 mmol) in 1,1,1,3,3,3-hexafluoroisopropanol (7.6 mL) was added Pd(OAc)2 (0.041 g, 0.182 mmol) and the reaction stirred for 45 minutes at room temperature. At this point the reaction was concentrated and purified directly by flash chromatography (0-40% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.71 (d, J=4.04 Hz, 1H) 6.87-7.32 (m, 3H) 6.65 (dd, J=16.17, 1.77 Hz, 1H) 6.26-6.43 (m, 1H) 1.94 (dd, J=6.69, 1.64 Hz, 3H) 1.60 (s, 9H).

Workup

  1. concentrationAt this point the reaction was concentrated
  2. custompurified directly by flash chromatography (0-40% EtOAc in heptanes)

Sources & evidence

ORD record
ord-1fa5a6c025874e7697d3284776a5a830
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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