Sodium Carbonate → HCID 44372061, compound

HRID 2305103Notes

Reaction equation

HRID 2305103 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[C:19]1[CH:20]=[C:21]([O:25][CH2:26][C@@H:27]2[CH2:31][CH2:30][CH2:29][N:28]2[CH3:32])[CH:22]=[N:23][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:19]2[CH:20]=[C:21]([O:25][CH2:26][C@@H:27]3[CH2:31][CH2:30][CH2:29][N:28]3[CH3:32])[CH:22]=[N:23][CH:24]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1562653,5-Bis-trifluoromethylphenylboronic acidHCID 112887213-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine

Product 1

HCID 44372061HCID 44372061, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,5-bis(trifluoromethyl)phenylboronic acid (0.55 g, 2.0 mmol, Lancaster Chem Co.) and 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (300 mg, 1.1 mmol) in toluene (5.0 mL) was added Pd(0) (25 mg) and Na2CO3 (1 mL of a 2 M solution), and the mixture was heated at reflux. The solvent was removed under vacuum, and the residue was purified by chromatography on silica gel to afford 225 mg of the title compound. MS (CI/NH3) m/z 405 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.83 (m, 3H), 2.08 (m, 1H), 2.36 (m, 1H), 2.54 (s, 3H), 2.78 (m, 1H), 3.17 (m, 1H), 4.10 (m, 2H), 7.42 (m, 1H), 7.92 (s, 1H), 8.00 (s, 2H), 8.42 (m, 1H), 7.92 (s, 1H), 8.00 (s, 2H), 8.42 (m, 1H), 8.48 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-354fcce3ada74783a41a7ad83142fd56
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

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