HCID 24985460, compound → HCID 24985462, compound

HRID 2101825Notes

Reaction equation

HRID 2101825 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]([CH2:18][OH:19])[N:6]2[CH2:13][C:14]([F:17])([F:16])[F:15]>CC#N.O=[Mn]=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]([CH:18]=[O:19])[N:6]2[CH2:13][C:14]([F:16])([F:17])[F:15]

Participants

4

Reactant 1

HCID 24985460HCID 24985460, compound

Product 1

HCID 24985462HCID 24985462, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-2-(hydroxymethyl)-1-(2,2,2-trifluoroethyl)-1H-indole-5-carbonitrile (0.07 g, 0.24 mmol) in MeCN (3 mL) was added activated MnO2 (0.21 g, 2.42 mmol). The mixture was stirred at rt for 2 h. Additional MnO2 (0.11 g, 1.21 mmol) was added and stirred for 1 h. The solids were filtered off and washed with EtOAc, CH2Cl2 and MeOH. The filtrate was concentrated in vacuo and the residue was purified by radial chromatography (2-30% EtOAc-hexanes gradient) to afford the title compound (0.046 g, 67% yield): MS (ES) m/z 285 (M−1).

Workup

  1. stirringstirred for 1 h
  2. filtrationThe solids were filtered off
  3. washwashed with EtOAc, CH2Cl2 and MeOH
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by radial chromatography (2-30% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-413972679b714f75bafc3e1f703d37dc
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

Loading…