HCID 24985463, compound → HCID 24985117, compound

HRID 1188319Notes

Reaction equation

HRID 1188319 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-ad44903e4a494196927f74013661eb0a
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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