Sodium Hydroxide → 4-(3-methyl-5-(pyridin-4-yl)-3H-1,2,3-triazol-4-yl)phenol

HRID 33933Notes

Reaction equation

HRID 33933 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([CH3:14])[N:12]=[N:11][C:10]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.[OH-].[Na+]>ClCCl>[CH3:14][N:13]1[C:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)=[C:10]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[N:11]=[N:12]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 685766994-(5-(4-methoxyphenyl)-1-methyl-1H-1,2,3-triazol-4-yl)pyridine

Product 1

HCID 1363758384-(3-methyl-5-(pyridin-4-yl)-3H-1,2,3-triazol-4-yl)phenolYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(5-(4-methoxyphenyl)-1-methyl-1H-1,2,3-triazol-4-yl)pyridine (170 mg, 0.64 mmol) in dichloromethane (5 mL) was treated at RT With boron tribromide (1.27 mL of 1M in dichloromethane) and the mixture was stirred overnight. Aqueous 1N NaOH (10 mL) was added, and after being stirred 1 h the mixture was extracted with dichloromethane (20 mL). The aqueous layer was acidified to pH 7 with 2N HCl, and extracted with ethyl acetate (2×15 mL). The extracts were dried with sodium sulfate and concentrated giving a yellow solid (142 mg, 88%). 1H NMR (CDCl3, 400 mHz) δ 1H NMR (CDCl3, 400 mHz) δ 8.39 (d, 2H, J=5-6 Hz), 7.49 (d, 2H, J=5-6 Hz), 7.09 (d, 2H, J=8.7 Hz), 6.95 (d, 2H, J=8.7 Hz), 3.87 (s, 3H). MS (AP−) 351 (M−H).

Workup

  1. stirringafter being stirred 1 h the mixture
  2. extractionwas extracted with dichloromethane (20 mL)
  3. extractionextracted with ethyl acetate (2×15 mL)
  4. dry with materialThe extracts were dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4f0ce3a5edef47d196e49309da819707
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

Loading…