Boron tribromide → 4-{N-[(6-hydroxy-benzothien-3-yl)methyl]-N-[1H-imidazol-1-yl-]amino}benzonitrile

HRID 446168Notes

Reaction equation

HRID 446168 reaction equation
[N:1]1([N:6]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:7][C:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17]C)=[CH:16][C:11]=3[S:10][CH:9]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:17][C:15]1[CH:14]=[CH:13][C:12]2[C:8]([CH2:7][N:6]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:9][S:10][C:11]=2[CH:16]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 694453164-{N-[1H-imidazol-1-yl]-N-[(6-methoxy-benzothien-3-yl)methyl]amino}benzonitrile

Product 1

HCID 694460384-{N-[(6-hydroxy-benzothien-3-yl)methyl]-N-[1H-imidazol-1-yl-]amino}benzonitrileYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-{N-[1H-imidazol-1-yl]-N-[(6-methoxy-benzothien-3-yl)methyl]amino}benzonitrile (0.50 g, 1.39 mmol) in 10 ml of methylene chloride is added at room temperature to a solution 1M of boron tribromide in methylene chloride (1.50 ml, 1.52 mmol). After 2 h at room temperature the mixture was hydrolysed with saturated aqueous NaHCO3, extracted with dichloromethane, dried over Na2SO4, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography on silica gel (toluene/dioxan:6/4) to give the expected product (0.30 g, 62%, powder). Crystallization with ethanol yielded white crystalsl (0.10 g, mp: 169° C.).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe crude product was purified by flash chromatography on silica gel (toluene/dioxan:6/4)

Sources & evidence

ORD record
ord-c315a170c60149839f53f5eb2a0326d2
Source dataset
uspto-grants-2013_07
Patent number
US08476455B2

Reaction notes

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