2,6-Di-tert-butyl-4-methylpyridine → HCID 69943982, compound

HRID 1934673Notes

Reaction equation

HRID 1934673 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:6][NH:7][C:8](=[O:23])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][C@H:19]([CH3:22])[CH2:20][OH:21].F[B-](F)(F)F.[CH3:34][O+](C)C.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:6][NH:7][C:8](=[O:23])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][C@H:19]([CH3:22])[CH2:20][O:21][CH3:34]

Participants

5

Reactant 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 9821702(R)-Xanthoanthrafil

Product 1

HCID 69943982HCID 69943982, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (R)-N-(3,4-dimethoxybenzyl)-2-(2-hydroxy-1-methylethylamino)-5-nitrobenzamide (200 mg) in 1,2-dichloroethane (10 mL) were added trimethyloxonium tetrafluoroborate (91.2 mg) and 2,6-di-tert-butyl-4-methylpyridine (158 mg), and the mixture was heated for 3 hours under reflux. The mixture was washed with 1N-hydrochloric acid, water, an aqueous saturated sodium bicarbonate solution and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (3:1 to 1:1). The obtained product was triturated with diisopropyl ether to give (R)-N-(3,4-dimethoxybenzyl)-2-(2-methoxy-1-methylethylamino)-5-nitrobenzamide as yellow powders (145 mg).

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. washThe mixture was washed with 1N-hydrochloric acid, water
  4. dry with materialThen, the resultant was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by a silica gel column chromatography
  7. washeluting with a mixture of hexane and ethyl acetate (3:1 to 1:1)
  8. customThe obtained product was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-b420d35826ad4a27a661f514b896b997
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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