Potassium Carbonate → HCID 21876300, compound

HRID 1454728Notes

Reaction equation

HRID 1454728 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]2[N:6]([C:11]3[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:9]([C:7]1[N:6]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[CH:13][CH:12]=2)[C:5]2[CH:20]=[CH:21][C:2]([C:2]3[CH:21]=[CH:20][CH:5]=[CH:4][CH:3]=3)=[CH:3][C:4]=2[N:8]=1)[CH3:10]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 21876465HCID 21876465, compound

Product 1

HCID 21876300HCID 21876300, compoundYield 53.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 2-[4-(5-bromo-2-ethyl-1H-benzimidazol-1-yl)phenyl]ethanol (step 4, 116 mg, 0.57 mmol) in 1,2-dimethoxyethane (DME, 6 ml) was added PhB (OH)2 (141 mg, 1.16 mmol), K2CO3 (240 mg, 1.75 mmol) and Pd(PPh3)4 (67 mg, 0.06 mmol). This mixture was stirred at 95° C. for 11 h. The reaction mixture was diluted with water and extracted with CH2Cl2 (4×10 ml). The organic layer was dried (MgSO4) and concentrated to give brown oil. This mixture was purified by SiO2 preparative TLC (hexane/ethyl acetate=1/5) to afford 52 mg (27%) of the title compound.

Workup

  1. extractionextracted with CH2Cl2 (4×10 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customto give brown oil
  5. customThis mixture was purified by SiO2 preparative TLC (hexane/ethyl acetate=1/5)

Sources & evidence

ORD record
ord-dc1a736257bd493692429e081ee88d45
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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