Potassium Carbonate → HCID 86729306, compound

HRID 1399919Notes

Reaction equation

HRID 1399919 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH3:10])[C:6]=2[CH:11]=1.[NH2:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:10][N:7]1[C:6]2[CH:11]=[C:2]([C:17]3[CH:18]=[C:13]([CH:14]=[CH:15][CH:16]=3)[NH2:12])[CH:3]=[CH:4][C:5]=2[N:9]=[CH:8]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 235376446-Bromo-1-methyl-1H-benzimidazole

Product 1

HCID 86729306HCID 86729306, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 6-bromo-1-methyl-1H-benzo[d]imidazole (500 mg, 2.37 mmol) in dioxane (10 mL) was added (3-aminophenyl)boronic acid (320 mg, 2.34 mmol), 2N K2CO3 (2 mL, 4 mmol) and PdCl2(dppf) (50 mg, 0.063 mmol). The reaction mixture was heated at 120° C. under microwave conditions for 30 min. The cooled mixture was concentrated under reduced pressure and the residue dissolved in ethyl acetate, washed with water with the separated organic layers being dried and concentrated to afford the desired product as a brown solid (300 mg, 56.7%). LCMS (m/z): 224.1 [M+H]+

Workup

  1. concentrationThe cooled mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water with the separated organic layers
  4. custombeing dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6cff7fe2468448da96a3bb940e1fbf7
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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