Sodium Carbonate → HCID 22961836, compound

HRID 2305156Notes

Reaction equation

HRID 2305156 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].[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O.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:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[CH:20]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 22872668HCID 22872668, compound

Product 1

HCID 22961836HCID 22961836, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromo-6-chloropyridine from Example 69a (1.5 g, 3.8 mmol), 2-thienylboronic acid (1.46 g, 11.5 mmol), 2 M Na2CO3 (5 mL) and Pd(0) (190 mg) were mixed together in toluene (20 mL), and the mixture was heated at reflux for 48 h. The mixture was cooled and extracted with EtOAc. The EtOAc was removed under reduced pressure, and the residue was chromatographed (silica gel; hexane/EtOAc, 4:1) to afford the title compound (340 mg, 32% yield): 1H NMR (CDCl3, 300 MHz) δ 1.47 (s, 9H), 1.84-2.11 (m, 4H), 3.31-3.46 (m, 2H), 3.89 (m, 1H), 4.05-4.26 (m, 2H), 7.14 (dd, 1H, J=4.5, 6.0 Hz), 7.42-7.50 (m, 2H), 8.05 (d, 1H, J=3.0 Hz), 8.07 (m, 1H); MS (CI/NH3) m/z 395 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 48 h
  3. temperatureThe mixture was cooled
  4. extractionextracted with EtOAc
  5. customThe EtOAc was removed under reduced pressure
  6. customthe residue was chromatographed (silica gel; hexane/EtOAc, 4:1)

Sources & evidence

ORD record
ord-6267ec8c4bc54b1fa16839e8391869ae
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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