Boron tribromide → HCID 90461113, compound

HRID 588846Notes

Reaction equation

HRID 588846 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([O:15]C)=[C:10]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:32])/[CH:26]=[CH:27]/[CH2:28][N:29]([CH3:31])[CH3:30])[CH2:21][CH2:20]2)=[O:18])[CH:9]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([Cl:14])=[CH:12][C:11]([OH:15])=[C:10]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:32])/[CH:26]=[CH:27]/[CH2:28][N:29]([CH3:30])[CH3:31])[CH2:21][CH2:20]2)=[O:18])[CH:9]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 90462363HCID 90462363, compound

Product 1

HCID 90461113HCID 90461113, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-1-(4-(2′,6-dichloro-4-methoxy-[1,1′-biphenyl]-3-carbonyl)piperazin-1-yl)-4-(dimethylamino)but-2-en-1-one (270 mg, 0.57 mmol) in DCM (5 mL) at −78° C., BBr3 (1.43 g, 5.7 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 2 h. The mixture was poured into ice-water, basified with the aqueous NaHCO3 to adjust the pH to 7 and then extracted with DCM (3×20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane/methanol=50:1) to afford the desired product (150 mg, 57% yield). 1HNMR (400 MHz, DMSO-d6) δ: 13.12 (s, 1H), 8.02 (s, 1H), 7.81 (s, 1H), 6.81 (m, 1H), 6.13 (dd, J=2.8, 16.8 Hz, 1H), 5.71 (dd, J=2.0, 10.4 Hz, 1H), 4.10 (s, 2H), 3.50-3.60 (m, 8H). ESI-MS m/z: 462.4[M+H]+.

Workup

  1. extractionextracted with DCM (3×20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-da06ee0f46f04de79b1a399ba71ac284
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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