Iodoethane → tert-Butyl 2-[N-(2-benzyloxy-5-bromophenethyl)-N-ethylamino]-5-pyridinecarboxylate

HRID 1106846Notes

Reaction equation

HRID 1106846 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:10]=1[CH2:11][CH2:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:16][N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:35][CH3:36]>CN(C=O)C.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:10]=1[CH2:11][CH2:12][N:13]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])=[CH:16][N:15]=1)[CH2:35][CH3:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 22675506tert-butyl 2-[N-(2-benzyloxy-5-bromophenethyl)amino]-5-pyridinecarboxylate

Product 1

HCID 22675480tert-Butyl 2-[N-(2-benzyloxy-5-bromophenethyl)-N-ethylamino]-5-pyridinecarboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl 2-[N-(2-benzyloxy-5-bromophenethyl)-amino]-5-pyridinecarboxylate (850 mg), and sodium hydride (110 mg, 50% dispersion in oil) in DMF (20 ml) was stirred for 15 minutes then iodoethane (150 ml) was added and the mixture stirred for 2 hours. The mixture was diluted with diethyl ether (50 ml) washed with water, dried (MgSO4), filtered through silica gel, evaporated and the residue redissolved in dichloromethane and evaporated to give tert-butyl 2-[N-(2-benzyloxy-5-bromophenethyl)-N-ethylamino]-5-pyridine carboxylate (800 mg).

Workup

  1. stirringthe mixture stirred for 2 hours
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through silica gel
  5. customevaporated
  6. dissolutionthe residue redissolved in dichloromethane
  7. customevaporated

Sources & evidence

ORD record
ord-f0520fde09614025bc39c382a85f8747
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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