Boron tribromide → HCID 59425735, compound

HRID 502254Notes

Reaction equation

HRID 502254 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:21]3[CH2:23][CH2:22]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19]C)[CH:11]=3)=[CH:4][CH:3]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:21]3[CH2:22][CH2:23]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([OH:19])[CH:11]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 59425315HCID 59425315, compound

Product 1

HCID 59425735HCID 59425735, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 2-(4-aminophenyl)-1-cyclopropyl-6-methoxyindole-3-carbonitrile (2.02 g, 6.7 mmol), prepared in example 1CG, step E, in dry DCM (30 mL), at −30° C., is added boron tribromide (8.35 g, 3.15 mL, 33.3 mmol). The mixture is stirred at −30° C. ˜−15° C. for 1.5 h and then brought to ambient temperature and stirred for 15 min. The mixture is poured into saturated NaHCO3 and ice and stirred for 1 h. The volatiles are removed on a rotovap and the precipitate is collected via filtration and washed with water and then dried under a stream of N2 to provide 2-(4-aminophenyl)-1-cyclopropyl-6-hydroxyindole-3-carbonitrile in quantitative yield.

Workup

  1. custombrought to ambient temperature
  2. stirringstirred for 15 min
  3. stirringstirred for 1 h
  4. customThe volatiles are removed on a rotovap
  5. filtrationthe precipitate is collected via filtration
  6. washwashed with water
  7. dry with materialdried under a stream of N2

Sources & evidence

ORD record
ord-62d65f22d5e342ad8b638da109cc105d
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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