Sodium Carbonate → HCID 44372369, compound

HRID 1780314Notes

Reaction equation

HRID 1780314 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:15]1[CH:16]=[C:17]([O:21][CH2:22][C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[CH3:28])[CH:18]=[N:19][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:15]2[CH:16]=[C:17]([O:21][CH2:22][C@@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3[CH3:28])[CH:18]=[N:19][CH:20]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 112887213-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine

Product 1

HCID 44372369HCID 44372369, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the compound from step 35a and 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (271 mg, 1.0 mmol) in toluene (5.0 mL) was added Pd(0) (25 mg) and Na2CO3 (1 mL of a 2M solution), and the mixture was heated at reflux for 4 hours. The solvent was removed under vacuum, and the residue was purified by chromatography on silica gel, eluting with 2 to 5% methanol in methylene chloride in a first column, followed by rechromatography, eluting with 0.1 to 1% ether in hexane, to afford 120 mg of the title compound. MS (CI/NH3) m/z 320 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.82, (m, 3H), 2.06 (m, 1H), 2.34 (m, 1H), 2.52 (s, 3H), 2.73 (m, 1H), 3.13 (m, 1H), 4.09 (m, 2H), 7.52 (m, 1H), 7.62, (m, 1H), 7.76 (m, 1H), 7.90 (m, 1H), 8.16 (m, 1H), 8.32 (m, 1H), 8.40 (m, 1H), 8.58 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on silica gel
  5. washeluting with 2 to 5% methanol in methylene chloride in a first column
  6. washeluting with 0.1 to 1% ether in hexane

Sources & evidence

ORD record
ord-34402ff2fc484279a97cac70e6ca2417
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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