Cesium carbonate → HCID 59426081, compound

HRID 506116Notes

Reaction equation

HRID 506116 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH:21]1(Br)[CH2:24][CH2:23][CH2:22]1>CN(C=O)C>[CH:21]1([N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:12]=3)[C:8]([C:13]#[N:14])=[CH:9]2)[CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 59425875HCID 59425875, compound

Product 1

HCID 59426081HCID 59426081, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

6-Ethoxy-1H-indole-3-carbonitrile (2.8 g, 15 mmol), prepared as shown in example 1A, step A, is combined with Cs2CO3 (11.6 g, 35.6 mmol), DMF (21 mL), and cyclobutyl bromide (1.73 mL, 17.9 mmol) in a capped tube. The reaction mixture is heated at 80° C. for 8 h. This is then quenched with H2O (200 mL) and is extracted with EtOAc. The EtOAc layer is backwashed with H2O, and then with brine. The organic phase is dried and concentrated. Purification by silica gel chromatography (hexanes/CH2Cl2, 50-100%) yields 1-cyclobutyl-6-ethoxy-1H-indole-3-carbonitrile (3.00 g, 83%) as a white solid.

Workup

  1. customThis is then quenched with H2O (200 mL)
  2. extractionis extracted with EtOAc
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (hexanes/CH2Cl2, 50-100%)

Sources & evidence

ORD record
ord-84ea75a592d14423a20b85dddc32fa2e
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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