Boron tribromide → HCID 90102531, compound

HRID 1052571Notes

Reaction equation

HRID 1052571 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([B:16]([OH:18])[OH:17])[CH:13]=[N:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([B:16]([OH:18])[OH:17])[CH:13]=[N:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 90102881HCID 90102881, compound

Product 1

HCID 90102531HCID 90102531, compoundYield 110.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(5-(4-Methoxybenzamido)pyridin-3-yl)boronic acid (300 mg, 0.79 mmol) was dissolved in dichloromethane (15 ml). A solution of boron tribromide (1M in dichloromethane, 3.93 mL, 3.93 mmol) was added dropwise and the reaction was stirred at room temperature overnight. The mixture was diluted with dichloromethane and washed with a solution of 4% sodium bicarbonate, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure. The product was purified by reverse phase using SP1® Purification System to give 225 mg (100% yield) of the title compound. Purity 98%.

Workup

  1. washwashed with a solution of 4% sodium bicarbonate, water, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe product was purified by reverse phase
  6. custom® Purification System

Sources & evidence

ORD record
ord-532fc988f9454964a45bd2b40bb4d1d8
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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