Sodium Bicarbonate → methyl 2-[N-(2-hydroxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate

HRID 427752Notes

Reaction equation

HRID 427752 reaction equation
C([O:8][C:9]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:10]=1[CH2:11][N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=1)[CH2:13][CH3:14])C1C=CC=CC=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CCCCCC>ClCCl>[Br:29][C:26]1[CH:27]=[CH:28][C:9]([OH:8])=[C:10]([CH:25]=1)[CH2:11][N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 22622546methyl 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylate

Product 1

HCID 11728230methyl 2-[N-(2-hydroxy-5-bromobenzyl)-N-ethylamino]pyridine-5-carboxylateYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]-5-pyridylcarboxylate (10.0 g, 22 mM) in dichloromethane (150 ml) was treated with boron trichloride dimethyl sulfide complex (40 ml, 2M, 80 mM). The reaction was stirred at ambient temperature for 48 hours. Saturated sodium bicarbonate solution was added and the layers were separated. The aqueous layer was washed with dichloromethane. The organic layers were combined, dried (MgSO4) and evaporated to give an off-white solid. The off-white solid was subjected to chromatography (diluted with ethyl acetate/hexane) to give the title compound (6.02 g, 75%).

Workup

  1. customthe layers were separated
  2. washThe aqueous layer was washed with dichloromethane
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an off-white solid

Sources & evidence

ORD record
ord-52046d389ec449d0927d736662fca8e8
Source dataset
uspto-grants-2001_11
Patent number
US06313148B1

Reaction notes

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