Boron tribromide → HCID 59191327, compound

HRID 1023893Notes

Reaction equation

HRID 1023893 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=2[O:18]C)[C:5]([NH2:20])=[CH:4][CH:3]=1.B(Br)(Br)Br.[NH4+].[Cl-]>ClCCl>[NH2:20][C:5]1[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=2[OH:18])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 24785923HCID 24785923, compound

Product 1

HCID 59191327HCID 59191327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 6-chloro-2-(2-methoxy-4-propyl phenoxy) pyridin-3-amine (0.1 mmol; 30 mg) under argon, in dichloromethane (2 mL), cooled to −78° C., was added BBr3 (0.5 mmol; 0.5 mL) dropwise. The reaction mixture was allowed to stir for 5 hr, with gradual warming to −20° C. At −20° C., the reaction was hydrolysed with saturated NH4Cl (4 mL), extracted with dichoromethane (3*10 mL). Combined organic phases dried over Na2SO4, concentrated in vacuo, to give the desired product as a light brown solid without further purification (27 mg 0.1 mmol; 97%).

Workup

  1. customAt −20° C.
  2. extractionextracted with dichoromethane (3*10 mL)
  3. dry with materialCombined organic phases dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52e0f2f6f51d4f13b1ea7afb5a9093ff
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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