Water → HCID 67355477, compound

HRID 1846149Notes

Reaction equation

HRID 1846149 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([OH:15])=[C:10]([CH3:16])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+].O>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([CH3:16])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 67353847HCID 67353847, compound

Product 1

HCID 67355477HCID 67355477, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution containing 1.18 g (5.50 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-hydroxy-4,6-dimethylpyridine (15) in 20 mL of anhydrous THF were added 1.20 mL (10.10 mmol) of benzyl bromide followed by 440 mg (11.00 mmol) of 60% sodium hydride suspension in mineral oil. The reaction mixture was stirred at room temperature under argon atmosphere overnight. The reaction mixture was poured into 150 mL of water and extracted with two portions of 100 mL of ethyl acetate. The combined organic solution was washed with a portion of 100 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 4:1 gave the expected product as light yellow oil: yield 1.42 g (84%). 1H-NMR (CDCl3) δ 6.98 (s, 1H), 5.91 (s, 2H), 4.94 (s, 2H), 2.58 (s, 3H), 2.37 (s, 3H), 2.17 (s, 6H); 13C-NMR (CDCl3) δ 152.02, 151.03, 146.64, 141.95, 136.73, 128.60, 128.33, 127.89, 121.94, 106.44, 74.59, 19.48, 16.18, 13.08.

Workup

  1. extractionextracted with two portions of 100 mL of ethyl acetate
  2. washThe combined organic solution was washed with a portion of 100 mL of brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column
  6. washElution with hexanes-ethyl acetate 4:1

Sources & evidence

ORD record
ord-06d7db4646d94bb093c70aefafbd5323
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

Loading…