Boron tribromide → HCID 44241532, compound

HRID 241605Notes

Reaction equation

HRID 241605 reaction equation
[Br:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)[C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[N:3]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)[C:4]2[C:9]([C:10]=1[C:11]#[N:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58378217HCID 58378217, compound

Product 1

HCID 44241532HCID 44241532, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Bromo-1-(4-methoxy-phenyl)-1H-indole-3-carbonitrile was dissolved in dry DCM and cooled to 0° C. 5 eq BBr3 (1.0 M solution in hexane) was added and the mixture was stirred over night. Still at 0° C., the reaction was quenched with the addition of MeOH. The mixture was diluted with H2O and the phases were partitioned. The organic phase was concentrated and the crude product purified on silica using n-heptane:EtOAc (4:1) as mobile phase. ES/MS m/z: 313, 315 (M+H), 311, 313 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.69 (m, 1H), 7.38-7.30 (m, 4H) and 7.16-7.10 (m, 3H).

Workup

  1. customStill at 0° C., the reaction was quenched with the addition of MeOH
  2. additionThe mixture was diluted with H2O
  3. customthe phases were partitioned
  4. concentrationThe organic phase was concentrated
  5. customthe crude product purified on silica

Sources & evidence

ORD record
ord-25778ec7060c4bd8978b3bcc22887768
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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