Cesium carbonate → 4-(3-Methyl-6-quinoxalinyl)benzonitrile

HRID 551547Notes

Reaction equation

HRID 551547 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[Cs+].Br[C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[C:26]([CH3:31])[CH:25]=[N:24]2>O.C1(C)C=CC=CC=1>[CH3:31][C:26]1[CH:25]=[N:24][C:23]2[C:28]([N:27]=1)=[CH:29][C:30]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)=[CH:21][CH:22]=2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 6142876-Bromo-2-methylquinoxalineHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 671046614-(3-Methyl-6-quinoxalinyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

4-Cyanophenylboronic acid (588 mg, 4.0 mmol), cesium carbonate (2.2 g, 7.0 mmol), and cesium fluoride (608 mg, 4.0 mmol) were combined in H2O (15 mL) and treated with the products from Example 61B (446 mg, 2.0 mmol) in toluene (10 mL) and heated at 80° C. for 3 hours. The reaction mixture was allowed to cool to room temperature and filtered through a pad of celite. The filtrate was partitioned between IPAc (60 mL) and H2O (50 mL). The organic layer was separated, washed with 20% brine, dried with Na2SO4, filtered, and the filtrate was concentrated under vacuum to provide the title compounds which were used in the next step without further purification. MS 246 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 8.71 (s, 1H), 8.69 (s, 1H), 8.02-8.20 (m, 4H), 7.84-7.90 (m, 2H), 7.70-7.76 (m, 8H), 2.73 (s, 6H); 13C NMR (400 MHz, CDCl3) δ 154.34, 154.10, 146.47, 147.17, 143.80, 142.93, 141.74, 140.62, 140.39, 140.18, 139.16, 132.49, 130.16, 129.74, 129.25, 128.71, 128.63, 128.06, 127.77, 127.74, 127.66, 127.59, 127.22, 126.73, 118.39, 118.37, 111.61, 111.51, 22.96.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through a pad of celite
  3. customThe filtrate was partitioned between IPAc (60 mL) and H2O (50 mL)
  4. customThe organic layer was separated
  5. washwashed with 20% brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-085bdd133cd64cc58587006900e7e3d2
Source dataset
uspto-grants-2011_05
Patent number
US07947711B2

Reaction notes

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