Sodium Carbonate → 4iodo-2,6-bis(N,N-bis(t-butoxycarbonylmethyl)aminomethyl)pyridine

HRID 2073918Notes

Reaction equation

HRID 2073918 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[N:5]=[C:4]([CH2:10]Br)[CH:3]=1.[NH:12]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[C:29](=[O:32])([O-:31])[O-].[Na+].[Na+]>C(#N)C>[I:1][C:2]1[CH:7]=[C:6]([CH2:8][N:12]([CH2:13][C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[N:5]=[C:4]([CH2:10][N:12]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:21][C:29]([O:31][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:32])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 4393691DI-T-Butyl iminodiacetateHCID 141457392,6-Bis(bromomethyl)-4-iodopyridine

Product 1

HCID 141457414iodo-2,6-bis(N,N-bis(t-butoxycarbonylmethyl)aminomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-iodo-2,6-bisbromomethylpyridine (0.59 g, 1.5 mmol) and di-t-butyl iminodiacetate (0.74 g, 3.0 mmol) in 40 mL of dry acetonitrile was added 1.59 g of sodium carbonate (15 mmol) and the mixture was stirred for 24 h at room temperature. Filtration and evaporation of the filtrate left a yellow oil. The oil was taken into 20 mL of chloroform, washed twice with 10 mL of water and dried with Na2SO4. Evaporation gave a yellowish oil which was purified by chromatographing on silica with toluene-ethanol (10:1).

Workup

  1. filtrationFiltration and evaporation of the filtrate
  2. waitleft a yellow oil
  3. washwashed twice with 10 mL of water
  4. dry with materialdried with Na2SO4
  5. customEvaporation
  6. customgave a yellowish oil which
  7. customwas purified by chromatographing on silica with toluene-ethanol (10:1)

Sources & evidence

ORD record
ord-68cba261ffa74c7fab9f1e514a84e5ec
Source dataset
uspto-grants-1990_04
Patent number
US04920195

Reaction notes

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