Boron tribromide → 3-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenol

HRID 1041902Notes

Reaction equation

HRID 1041902 reaction equation
B(Br)(Br)Br.C([O:12][C:13]1[CH:14]=[C:15]([C:19]2[N:23]3[CH:24]=[C:25]([Br:28])[CH:26]=[CH:27][C:22]3=[N:21][N:20]=2)[CH:16]=[CH:17][CH:18]=1)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:28][C:25]1[CH:26]=[CH:27][C:22]2[N:23]([C:19]([C:15]3[CH:14]=[C:13]([OH:12])[CH:18]=[CH:17][CH:16]=3)=[N:20][N:21]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 575414023-(3-Benzyloxy-phenyl)-6-bromo-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 669777183-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenolYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1 M in DCM, 13.1 mL, 13.1 mmol) was added slowly to a stirred solution of 3-(3-benzyloxy-phenyl)-6-bromo-[1,2,4]triazolo[4,3-a]pyridine (1 g, 2.63 mmol) in DCM (5 mL) at −78° C. The reaction was allowed to warm up to RT, stirred for 24 h, and treated with sat. NaHCO3 solution until pH>7. The product was extracted with DCM:MeOH 9:1 (mL), dried (MgSO4), and concentrated in vacuo. Purification of the crude residue by FCC (DCM:MeOH, 1:0 to 9:1) afforded the title compound (350 mg, 46%) as a yellow solid. LCMS (Method 2): Rt 2.65 min, m/z 290 and 292 [MH+].

Workup

  1. extractionThe product was extracted with DCM:MeOH 9:1 (mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification of the crude residue by FCC (DCM:MeOH, 1:0 to 9:1)

Sources & evidence

ORD record
ord-89fd52af7fa14a10a27e5fc357ac536b
Source dataset
uspto-grants-2013_10
Patent number
US08557797B2

Reaction notes

Loading…