Potassium Cyanide → HCID 69308201, compound

HRID 860485Notes

Reaction equation

HRID 860485 reaction equation
Br[CH2:2][C:3]1[C:4]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:5]([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=2)[C:6]2[N:7]([C:9]([CH2:12][CH3:13])=[CH:10][CH:11]=2)[N:8]=1.[C-:30]#[N:31].[K+]>CN(C)C=O>[Br:20][C:18]1[CH:19]=[C:14]([C:5]2[C:6]3[N:7]([C:9]([CH2:12][CH3:13])=[CH:10][CH:11]=3)[N:8]=[C:3]([CH2:2][C:30]#[N:31])[C:4]=2[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:15]=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 69311530HCID 69311530, compound

Product 1

HCID 69308201HCID 69308201, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 5-[2-(bromomethyl)-4-(5-bromo-3-pyridinyl)-7-ethylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate (70.0 mg) and potassium cyanide (13.1 mg) in N,N-dimethylformamide (1 mL) was stirred for 28 hours at room temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water (two times), brine, dried over magnesium sulfate, and evaporated to give ethyl 5-[4-(5-bromo-3-pyridinyl)-2-(cyanomethyl)-7-ethylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate as an yellow gum (28.8 mg, 45.9%).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water (two times), brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-aa0e6550eb95406b938b3cc7fc601485
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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