Cesium carbonate → HCID 66667121, compound

HRID 1620352Notes

Reaction equation

HRID 1620352 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[N:13][C:14]([CH:18]2[CH2:20][CH2:19]2)=[C:15]([Cl:17])[CH:16]=1)[C:5]#[N:6].[CH3:21][O:22][C:23]1[C:28](B(O)O)=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[Cl:17][C:15]1[CH:16]=[C:11]([O:10][C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=2[C:28]2[C:23]([O:22][CH3:21])=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:12]=[N:13][C:14]=1[CH:18]1[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 66666781HCID 66666781, compound

Product 1

HCID 66667121HCID 66667121, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

3-bromo-4-(5-chloro-6-cyclopropylpyridin-3-yloxy)benzonitrile (Preparation 38, 485 mg, 1.37 mmol), 2-methoxypyridin-3-ylboronic acid (233 mg, 1.53 mmol) and cesium carbonate were suspended in dioxane (6 mL) and water (3 mL). The suspension was degassed 20 minutes with nitrogen then tetrakis-triphenylphosphinepalladium (80 mg, 0.07 mmol) were added and the reaction mixture was heated overnight at 75° C. The solution was concentrated in vacuo to a quarter of the volume then diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography to afford the title compound as a foam (478 mg, 91%).

Workup

  1. customThe suspension was degassed 20 minutes with nitrogen
  2. concentrationThe solution was concentrated in vacuo to a quarter of the volume
  3. additionthen diluted with water (20 mL)
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9afcd7090601444e96e494ac7d79a94a
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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