Dimethylformamide → Butyl 6-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridazine-3-carboxylate

HRID 840310Notes

Reaction equation

HRID 840310 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=C[C:14]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH:34]([CH3:36])[CH3:35].C[N:38](C)C=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH2:33][CH:34]([CH3:36])[CH3:35])=[C:6]([CH:24]=1)[CH2:7][N:8]([C:11]1[N:16]=[N:38][C:14]([C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[CH:13][CH:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 65551-Bromo-2-methylpropane2×HCID 11430Potassium Carbonate2×HCID 22622549Butyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-3-carboxylate

Product 1

HCID 22622534Butyl 6-[N-(5-bromo-2-(2-methylpropoxy)benzyl)-N-ethylamino]pyridazine-3-carboxylateYield 98%

Procedure

Butyl 6-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-3-carboxylate (reference example 3) (1.12 g, 2.76 mmol) in dimethylformamide (16 ml) was treated with potassium carbonate followed by 1-bromo-2-methylpropane (0.16 ml, 770 mg, 5.6 mmol) and stirred at ambient temperature overnight. TLC showed reaction to be incomplete so further potassium carbonate (1.12 g) and 1 -bromo-2-methylpropane were added and the mixture stirred at ambient temperature over two days. The mixture was then evaporated to low bulk and the residue purified directly by MPLC to give the title compound as a colourless gum (1.26 g, 98%).

Workup

  1. customreaction
  2. additionwere added
  3. stirringthe mixture stirred at ambient temperature over two days
  4. customThe mixture was then evaporated to low bulk
  5. customthe residue purified directly by MPLC

Sources & evidence

ORD record
ord-a14614a4f5f148f6bffb4515daad728f
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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