Potassium Iodide → HCID 123949802, compound

HRID 717101Notes

Reaction equation

HRID 717101 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]2[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]2)=[CH:5][CH:4]=1.[CH3:18][C:19]1[NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.[I-].[K+].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[CH3:18][C:19]1[N:23]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([B:9]3[O:17][C:14]([CH3:16])([CH3:15])[C:11]([CH3:13])([CH3:12])[O:10]3)=[CH:5][CH:4]=2)[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[N:20]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 119842-MethylbenzimidazoleHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 123949802HCID 123949802, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-bromomethylphenylboronic acid pinacol ester (564 mg, 1.90 mmol) in acetone (19 mL) was added 2-methylbenzimidazole (377 mg, 2.85 mmol), potassium iodide (16 mg, 0.095 mmol) and K2CO3 (394 mg, 2.85 mmol) and the reaction mixture heated at 60° C. for 3.25 h. The reaction mixture was diluted with H2O and extracted with EtOAc (×2). The organic layers were combined, dried (phase separation cartridge) and concentrated in vacuo. The crude material was purified by reverse phase preparative HPLC-MS to afford 2-Methyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]1H-benzoimidazole as an off-white solid (234 mg, 35%).

Workup

  1. extractionextracted with EtOAc (×2)
  2. customdried
  3. custom(phase separation cartridge)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-628d8f0532dc4d829fdcbb36d8d413c5
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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