Boron tribromide → 7-Ethyl-5-({4-[(1E)-3-(4-methyl-1-piperazinyl)-3-oxo-1-propen-1-yl]phenyl}oxy)-6-phenyl-2-naphthalenol

HRID 1992858Notes

Reaction equation

HRID 1992858 reaction equation
[CH2:1]([C:3]1[C:4]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[O:25])=[CH:18][CH:17]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13]C)=[CH:8][CH:7]=2)[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([OH:13])=[CH:10]2)=[C:5]([O:15][C:16]2[CH:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[O:25])=[CH:20][CH:21]=2)[C:4]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH3:2]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 685367431-[(2E)-3-(4-{[3-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoyl]-4-methylpiperazine

Product 1

HCID 116346097-Ethyl-5-({4-[(1E)-3-(4-methyl-1-piperazinyl)-3-oxo-1-propen-1-yl]phenyl}oxy)-6-phenyl-2-naphthalenolYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[(2E)-3-(4-{[3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoyl]-4-methylpiperazine (61) (83 mg, 0.17 mmol) in reagent grade CH2Cl2 (8 mL) at −10° C. was added BBr3 (97 μL, 1.03 mmol) dropwise. The mixture was then stirred at 0° C. to 5° C. for 6 h, poured into saturated aqueous NaHCO3 (30 mL) and extracted with CH2Cl2. The combined extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a brown solid. The crude product was triturated with hot hexanes (containing small amount of CH2Cl2 and MeOH) to give 44 mg (55%) of the title compound (63) as an off-white solid. mp 195-196° C. 1H NMR (400 MHz, CH3OH-d4): δ 1.07 (t, J=7.5 Hz, 3H), 2.31 (s, 3H), 2.47 (br s, 4H), 2.54 (q, J=7.5 Hz, 2H), 3.70 (br s, 4H), 6.54 (d, J=8.8 Hz, 2H), 6.91 (d, J=15.4 Hz, 1H), 6.96 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.10-7.17 (m, 3H), 7.18-7.28 (m, 3H), 7.37 (d, J=8.6 Hz, 2H), 7.44 (d, J=15.4 Hz, 1H), 7.52 (s, 1H), 7.60 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 493 (M+H)+, m/z 491 (M−H)−. HRMS (EI) Calc for C32H32 N2O3: 493.2491 (M+•). Found: 493.2500.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe combined extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give the crude product as a brown solid
  8. customThe crude product was triturated with hot hexanes (containing small amount of CH2Cl2 and MeOH)

Sources & evidence

ORD record
ord-ff9876cc01d84a6b909d1262bba6c753
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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