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

HRID 540630Notes

Reaction equation

HRID 540630 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 (%)=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-42dcded92cd848568eee8de9fc0086d4
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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