Sodium Carbonate → HCID 22961837, compound

HRID 365870Notes

Reaction equation

HRID 365870 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:22])=[C:19](Br)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:16]=[N:17][C:18]([Cl:22])=[C:19]([C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=2)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 22872668HCID 22872668, compound

Product 1

HCID 22961837HCID 22961837, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromo-6-chloropyridine (1.64 g, 4.20 mmol) and 4-chlorophenylboronic acid (620 mg, 3.9 mmol.) in toluene (20 mL) was added Pd(0) (97 mg) and Na2CO3 (5 mL of a 2 M solution), and the mixture was heated at reflux for 16 h. The reaction mixture was quenched with saturated NaHCO3 solution and extracted with Et2O. The solvent was removed under vacuum, and the residue was chromatographed (silica gel; EtOAc/hexane, 1:4) to afford the title compound (430 mg, 24% yield): 1H NMR (CDCl3, 300 MHz) δ1.45 (s, 9H), 1.83-2.00 (m, 4H), 3.30-3.45 (m, 2H), 4.00 (m, 1H), 4.06-4.25 (m, 2H), 7.36-7.46 (m, 5H), 8.10 (s, 1H); MS (CI/NH3) m/z 423 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. customThe reaction mixture was quenched with saturated NaHCO3 solution
  4. extractionextracted with Et2O
  5. customThe solvent was removed under vacuum
  6. customthe residue was chromatographed (silica gel; EtOAc/hexane, 1:4)

Sources & evidence

ORD record
ord-0ecd46e5b3454eaab98fbbd0bdd68189
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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