Sodium Carbonate → HCID 66793903, compound

HRID 1623560Notes

Reaction equation

HRID 1623560 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]2[N:6]([CH3:11])[C:7](=[O:10])[N:8]([CH3:9])[C:4]=2[CH:3]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:11][N:6]1[C:5]2[CH:12]=[CH:13][C:2]([C:16]3[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=3)=[CH:3][C:4]=2[N:8]([CH3:9])[C:7]1=[O:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 470034475-Bromo-1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-one

Product 1

HCID 66793903HCID 66793903, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-Bromo-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (121 mg, 0.5 mmol), 3-pyridyl boronic acid (68 mg, 0.55 mmol), polymer-supported Pd(PPh3)4 (0.09 mmol/g, 278 mg, 0.025 mmol) and Na2CO3 (2 M in water, 0.55 mL, 1.1 mmol) in DME (3.3 mL) was heated to reflux for 1 hr. After filtration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-7.5%) and yielded the title compound (38 mg). MS (ESI) m/z 240.0 (M+H), retention time 1.00 min. 1H NMR (400 MHz, CD2Cl2) δ ppm 3.47 (s, 3H), 3.49 (s, 3H), 7.13 (d, J=8.1 Hz, 1H), 7.25 (s, 1H), 7.38-7.40 (m, 1H), 7.41-7.44 (m, 1H), 7.95-7.98 (m, 1H), 8.60 (m, 1H), 8.90 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hr
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-7.5%)

Sources & evidence

ORD record
ord-0820e4f295824495bb2dc66b6268e9e7
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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