Sodium hydride → HCID 68802498, compound

HRID 860505Notes

Reaction equation

HRID 860505 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[N:12]([C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)[N:13]=[C:14]([CH2:23][OH:24])[C:15]=2[CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])[CH:7]=[CH:8][CH:9]=1.Br.Br[CH2:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:11]3[N:12]([C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)[N:13]=[C:14]([CH2:23][O:24][CH2:32][C:33]3[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=3)[C:15]=2[CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127522194-(Bromomethyl)pyridine hbrHCID 68802482HCID 68802482, compound

Product 1

HCID 68802498HCID 68802498, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium hydride (93.1 mg) in DMF (4 mL) was added ethyl 3-[4-(3-chlorophenyl)-7-ethyl-2-(hydroxymethyl)pyrrolo[1,2-b]pyridazin-3-yl]propanoate (150 mg) under ice water cooling and the mixture was stirred at this temperature for 1 hour. To this was added 4-(bromomethyl)pyridine hydrobromide (196 mg) and the mixture was stirred for 1 hour at ambient temperature. The reaction was quenched by adding water. The mixture was extracted with CHCl3. The organic layer was washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of CHCl3-MeOH=30-1 to give 3-{4-(3-chlorophenyl)-7-ethyl-2-[(4-pyridinylmethoxy)methyl]pyrrolo[1,2-b]pyridazin-3-yl}propanoic acid (18 mg) as a yellow solid.

Workup

  1. stirringthe mixture was stirred for 1 hour at ambient temperature
  2. customThe reaction was quenched
  3. additionby adding water
  4. extractionThe mixture was extracted with CHCl3
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a mixture of CHCl3-MeOH=30-1

Sources & evidence

ORD record
ord-989fb7efeeab45b683e2710fccd381ff
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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