Cesium carbonate → HCID 59426081, compound

HRID 252603Notes

Reaction equation

HRID 252603 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-c1fcd1dcc38a4a09b43320552afb3f3e
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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