Boron tribromide → HCID 9927455, compound

HRID 1437453Notes

Reaction equation

HRID 1437453 reaction equation
[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C)[CH:11]=2)[CH:8]=[C:7]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:1]([N:4]1[CH2:5][CH2:6][C:7]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])=[CH:8][CH:9]1[C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57941180HCID 57941180, compound

Product 1

HCID 9927455HCID 9927455, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

1-Acetyl-4-(2,5-difluorophenyl)-6-(3-methoxyphenyl)-1,2,3,6-tetrahydropyridine (1-6,20 mg, 0.06 mmol) was dissolved in CH2Cl2 (1 mL) and treated with BBr3 (0.58 mL, 1M in CH2Cl2, 0.6 mmol). The reaction was stirred 6 h at 25° C. until completion. The reaction solution was washed with 5% NH4Cl (aq.), dried with MgSO4 and filtered. Following concentration under reduced pressure, the crude was purified via reverse phase column chromatography (CH3CN/H2O/0.1% TFA gradient) to provide 3-[1-Acetyl-4-(2,5-difluorophenyl)-1,2,5,6-tetrahydropyridin-2-yl]phenol (1-7). δ 7.26 (m, 2H), 6.96 (m, 5H), 6.38 (s, 1H); 6.15 (m, 1H), 3.79 (dd, J=13.7, 4.9 Hz, 1H), 3.42 (dt, J=11.0, 3.7 Hz, 1H); 2.75 (m, 1H); 2.42 (dd, J=16.0, 1.0 Hz, 1H), 2.21 (s, 3H); MS 330.0 found, 330.4 (M+H+) required.

Workup

  1. washThe reaction solution was washed with 5% NH4Cl (aq.)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentration under reduced pressure
  5. customthe crude was purified via reverse phase column chromatography (CH3CN/H2O/0.1% TFA gradient)

Sources & evidence

ORD record
ord-f1f9362236da464885dba953a834a993
Source dataset
uspto-grants-2009_11
Patent number
US07622489B2

Reaction notes

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