HCID 24985463, compound → HCID 24985117, compound

HRID 913392Notes

Reaction equation

HRID 913392 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5](/[CH:18]=[CH:19]\[CH3:20])[N:6]2[CH2:13][C:14]([F:17])([F:16])[F:15].ClC1C(C#N)=CC=C2C=1C=C(/C=C/C)N2CC(F)(F)F>CCOC(C)=O.O=[Pt]=O>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH2:18][CH2:19][CH3:20])[N:6]2[CH2:13][C:14]([F:15])([F:16])[F:17]

Participants

5

Reactant 2

HCID 24985463HCID 24985463, compoundHCID 24985464HCID 24985464, compound

Product 1

HCID 24985117HCID 24985117, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-2-[(1Z)-1-propen-1-yl]-1-(2,2,2-trifluoroethyl)-1H-indole-5-carbonitrile (Example 13) and 4-chloro-2-[(1E)-1-propen-1-yl]-1-(2,2,2-trifluoroethyl)-1H-indole-5-carbonitrile (Example 14) (˜2:1 mixture, 0.014 g, 0.046 mmol) in EtOAc (2 mL) under N2, was added PtO2 (4 mg) and the mixture was hydrogenated under balloon pressure for 15 min. The catalyst was filtered off and washed with EtOAc and MeOH. The filtrate was concentrated and the residue was purified by radial chromatography (2-30% EtOAc-hexanes gradient) to afford the title compound (0.013 g, 92% yield): MS (ES) m/z 301 (M+1).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with EtOAc and MeOH
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by radial chromatography (2-30% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-afaf735413bc43418cbd2d9a75fcb35f
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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