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

HRID 1604380Notes

Reaction equation

HRID 1604380 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-carboxylate

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-d9e4b4a25e65493abe288ff49310befc
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

Loading…