1-Acetoxy-2-bromoethane → HCID 69311544, compound

HRID 860469Notes

Reaction equation

HRID 860469 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:20]([CH3:22])[CH3:21])[C:9]([CH2:18][OH:19])=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1.[H-].[Na+].[C:25](OCCBr)(=[O:27])[CH3:26]>CN(C)C=O>[C:25]([O:19][CH2:18][C:9]1[C:8]([CH:20]([CH3:22])[CH3:21])=[N:7][N:6]2[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 54440531HCID 54440531, compound

Product 1

HCID 69311544HCID 69311544, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl)methanol (40 mg) in N,N-dimethylformamide (1 mL) was added 40% sodium hydride in oil (5.5 mg) in an ice-water bath. After 20 minutes, to the mixture was added 2-bromoethyl acetate (31 mg) at the temperature. After 15 minutes, the reaction mixture was stirred at ambient temperature for 5 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water three times and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by p-TLC (hexane-ethyl acetate=10-1) to give [7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]methyl acetate as a pale yellow solid (42 mg).

Workup

  1. waitAfter 15 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water three times and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by p-TLC (hexane-ethyl acetate=10-1)

Sources & evidence

ORD record
ord-dc5613c94bbb4cd38e66aec4c618e697
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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