Sodium Carbonate → HCID 59374221, compound

HRID 473610Notes

Reaction equation

HRID 473610 reaction equation
Br[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:16][C:17]1[CH:22]=[C:21](B(O)O)[CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[Na+].[Na+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(#N)C.O>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:3]2[C:2]([C:21]3[CH:20]=[CH:19][N:18]=[C:17]([CH3:16])[CH:22]=3)=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 41926642-Methylpyridine-4-boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 59374031HCID 59374031, compound

Product 1

HCID 59374221HCID 59374221, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a sealed tube, under nitrogen was added 3-bromo-2-(4-chlorophenoxy)-pyridine (7 g, 25 mmol), 2-methylpyridin-4-ylboronic acid (3.4 g, 25 mmol), sodium carbonate (7.8 g, 74 mmol), S-phos (1 g, 2.5 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), and 180 mL of acetonitrile/water (5:1). The resulting mixture was heated to 75 C overnight. The reaction mixture was filtered to remove the solids and concentrated by rotovap. The residue was diluted with DCM and washed with brine. The organic layer was dried over Na2SO4 and concentrated. The solid and the residue was combined and purified by silica gel chromatography (0-10% MeOH/DCM) to afford 2-(4-chlorophenoxy)-3-(2-methylpyridin-4-yl)pyridine as solid. MS (ESI, pos. ion) m/z: 296.8 (M+1).

Workup

  1. temperatureThe resulting mixture was heated to 75 C overnight
  2. filtrationThe reaction mixture was filtered
  3. customto remove the solids
  4. concentrationconcentrated by rotovap
  5. additionThe residue was diluted with DCM
  6. washwashed with brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-7a8cb59c1f3a486295d403f230a4d4b9
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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