Cesium carbonate → HCID 57800261, compound

HRID 1188581Notes

Reaction equation

HRID 1188581 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2)[CH2:2][CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:26][C:27]1[N:31]=[C:30]([C:32]2[C:33]([S:38][CH3:39])=[N:34][CH:35]=[CH:36][CH:37]=2)[O:29][N:28]=1>C(#N)C>[CH3:39][S:38][C:33]1[C:32]([C:30]2[O:29][N:28]=[C:27]([CH2:26][N:5]3[C:6]4[C:11](=[C:10]([C:13]([F:15])([F:16])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=4)[CH:12]=[C:4]3[CH2:1][CH2:2][CH3:3])[N:31]=2)=[CH:37][CH:36]=[CH:35][N:34]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27967603-[3-(Chloromethyl)-1,2,4-oxadiazol-5-yl]-2-(methylsulfanyl)pyridineHCID 674051552-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 57800261HCID 57800261, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 153A) (0.100 g, 0.396 mmol) in anhydrous acetonitrile (20 mL) was added Cs2CO3 (1.30 g, 4.00 mmol) and 3-[3-(chloromethyl)-1,2,4-oxadiazol-5-yl]-2-(methylthio)pyridine (0.170 g, 0.594 mmol). The mixture was heated under N2, for 2 h. Upon cooling, the mixture was partitioned between EtOAc and water. The organic phase was separated, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-20% EtOAc-hexanes gradient) to afford a pure product (0.152 g, 84% yield): MS (ES) m/z 458 (M+).

Workup

  1. temperatureThe mixture was heated under N2, for 2 h
  2. temperatureUpon cooling
  3. customthe mixture was partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (0-20% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-0c1e3b2ba2de4bab9b2a8d43f83e0d6d
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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