Acetonitrile → HCID 52984061, compound

HRID 1524182Notes

Reaction equation

HRID 1524182 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:10][CH2:11][CH2:12]Br.C(#N)C>C(Cl)Cl>[Cl:10][CH2:11][CH2:12][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 78491-Bromo-2-ChloroethaneHCID 10328Indoline

Product 1

HCID 52984061HCID 52984061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A microwave vial was charged with indoline (0.5 g, 4.19 mmol), 2-chloro-1-bromoethane (0.502 ml, 6.25 mmol), TEA (0.7 ml, 6.25 mmol) and acetonitrile (10 ml). The vial was irradiated with microwaves for 1 hour at 80° C. The mixture was diluted with DCM and washed with water (1×10 ml). The organic layer was dried and concentrated and the residue was purified by flash column chromatography (silica, Hexane/EtOAc 95:5 to 0:1). The product was isolated as a violet solid (400 mg; 52%).

Workup

  1. customThe vial was irradiated with microwaves for 1 hour at 80° C
  2. washwashed with water (1×10 ml)
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customthe residue was purified by flash column chromatography (silica, Hexane/EtOAc 95:5 to 0:1)
  6. customThe product was isolated as a violet solid (400 mg; 52%)

Sources & evidence

ORD record
ord-beddc61be5534982a0ac35993c167921
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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