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

HRID 355808Notes

Reaction equation

HRID 355808 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[C:21]([Br:23])[CH:20]=[CH:19][C:18]=2[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH2:35][CH3:36]>CN(C=O)C.C(OCC)C>[CH2:25]([O:24][C:18]1[CH:19]=[CH:20][C:21]([Br:23])=[CH:22][C:17]=1[CH2:16][CH2:15][N:14]([C:11]1[CH:10]=[CH:9][C:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:13][N:12]=1)[CH2:35][CH3:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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-butyl2-[N-(2-benzyloxy-5-bromophenethyl)-amino]-5-pyridinecarboxylate (850 mg), and sodium hydride (101 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 re-dissolved 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 re-dissolved in dichloromethane
  7. customevaporated

Sources & evidence

ORD record
ord-c6182d114d2c49faa213a2e990326f86
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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