Sodium Carbonate → HCID 22872657, compound

HRID 2305131Notes

Reaction equation

HRID 2305131 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[N:6][C:7]=1[Cl:8].[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>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:3]=[C:4]([O:9][CH2:10][C@H:11]3[CH2:15][CH2:14][CH2:13][N:12]3[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:5]=[N:6][C:7]=2[Cl:8])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 22872666HCID 22872666, compound

Product 1

HCID 22872657HCID 22872657, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-6-chloro-3-(1-BOC-2-(R)-pyrrolidinylmethoxy)pyridine from Example 69a (460 mg, 1.2 mmol) and 4-chlorophenylboronic acid (225 mg, 1.44 mmol) in toluene (10 mL) was added Pd(0) (40 mg) and Na2CO3 (1.2 mL of a 2 M solution), and the mixture was heated at reflux for 1.5 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on a silica gel column, eluting with hexane:Et2O 100:10-100:30 to afford ofthe title compound (345 mg, 68% yield). MS (CI/NH3) m/z 423 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.45 (s, 9H), 1.89 (m, 2H), 2.03 (m, 2H), 3.37 (m, 2H), 4.00 (m, 1H), 4.15 (m, 2H), 7.42 (m, 6H), 8.10 (m, 2H)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on a silica gel column
  5. washeluting with hexane:Et2O 100:10-100:30

Sources & evidence

ORD record
ord-84c4cc48c9194bcfaf6f3aab5713816f
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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