Boron tribromide → N-(4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)phenyl)acetamide

HRID 919544Notes

Reaction equation

HRID 919544 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[C:13]1[N:14]([CH3:18])[N:15]=[CH:16][CH:17]=1.B(Br)(Br)Br>ClCCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][C:4]=1[C:13]1[N:14]([CH3:18])[N:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59514683(N-[4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)phenyl])acetamide

Product 1

HCID 135697938N-(4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)phenyl)acetamideYield 21%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of N-[4-methoxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-acetamide (2.57 g, 10.48 mmol) in 1,2-dichloroethane (75 mL) was added BBr3 (10 mL, 106 mmol) and stirred for three hours. The nonhomogeneous suspension was heated to reflux for 15 minutes and then cooled to room temperature. The reaction was quenched by slow addition of methanol. The resulting material was purified by HPLC. The product was dried in vacuo to afford N-[4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]acetamide as a white solid (508 mg, 21%). LCMS m/z (%)=232 (M+H, 100), 1H NMR (400 MHz, DMSO-d6) δ: 9.77 (bs, 1H), 9.66 (bs, 1H), 7.44-7.40 (m, 3H), 6.89 (d, J=8.85 Hz, 1H), 6.37 (d, J=1.81 Hz, 1H), 3.66 (s, 3H), 1.99 (s, 3H).

Workup

  1. temperatureThe nonhomogeneous suspension was heated
  2. temperatureto reflux for 15 minutes
  3. customThe reaction was quenched by slow addition of methanol
  4. customThe resulting material was purified by HPLC
  5. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-805cfe446ac74402b23fd28d0929783a
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

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