1-(5-(2H-1,2,3,4-Tetrazol-5-Yl)(1H-Indazol-3-Yl))-2-Methoxybenzene → 2-(5-(2h-1,2,3,4-Tetrazol-5-yl)-1h-indazol-3-yl)phenol

HRID 1349679Notes

Reaction equation

HRID 1349679 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21]C>B(Br)(Br)Br>[N:4]1[NH:3][N:2]=[N:1][C:5]=1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21]

Participants

3

Reactant 1

HCID 224800881-(5-(2H-1,2,3,4-Tetrazol-5-Yl)(1H-Indazol-3-Yl))-2-Methoxybenzene

Product 1

HCID 1360112662-(5-(2h-1,2,3,4-Tetrazol-5-yl)-1h-indazol-3-yl)phenolYield 6.3%

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

The compound of Example 161 (0.050 g, 0.17 mmol) was suspended in 1 mL of boron tribromide (1.0 M commercial solution in dichloromethane). The reaction mixture was stirred at room temperature in a closed system for 4 days to achieve completion. The product was then collected by filtration and washed with small portions of dichloromethane. Trituration in a few mL of tetrahydrofuran and filtration did not afford satisfactory purity. Final purification by preparative HPLC (30–80% acetonitrile in water, 20 mm) afforded 3 mg of pure product. (6% yield): 1H NMR (DMSO-d6) δ 13.6 (s, 1H), 10.3 (s, 1H), 8.7 (s, 1H), 8.1 (d, 1H), 7.8 (t, 2H), 7.3 (t, 1H), 7.08–7.00 (m, 2H); ES-MS (m/z) 279 [M+1]+.

Workup

  1. filtrationThe product was then collected by filtration
  2. washwashed with small portions of dichloromethane
  3. filtrationTrituration in a few mL of tetrahydrofuran and filtration
  4. customdid not afford satisfactory purity
  5. customFinal purification by preparative HPLC (30–80% acetonitrile in water, 20 mm)

Sources & evidence

ORD record
ord-a825d66ac8a749bbb870fa67436adc27
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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