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

HRID 1170372Notes

Reaction equation

HRID 1170372 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-105843ed31684349af343e7136ee55d2
Source dataset
uspto-grants-2010_11
Patent number
US07825254B2

Reaction notes

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