HCID 69311399, compound → HCID 69311335, compound

HRID 2250653Notes

Reaction equation

HRID 2250653 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]2[C:12]3[N:13]([C:23]([CH2:26][CH3:27])=[CH:24][CH:25]=3)[N:14]=[C:15]([CH3:22])[C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5]>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:9]([C:11]2[C:12]3[N:13]([C:23]([CH2:26][CH3:27])=[CH:24][CH:25]=3)[N:14]=[C:15]([CH3:22])[C:16]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

3

Reactant 1

HCID 69311399HCID 69311399, compound

Product 1

HCID 69311335HCID 69311335, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-4-[3-(ethoxycarbonyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-4-yl]benzoic acid (50.0 mg) in tetrahydrofuran (1 mL) was added a solution of 1 M borane-tetrahydrofuran complex (0.348 mL) in an ice bath. After stirring for 2 hours at room temperature, additional solution of the borane-tetrahydrofuran complex (0.348 mL) was added. The mixture was stirred for 15 hours at room temperature. The mixture was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with water, saturated sodium bicarbonate, and brine, dried over magnesium sulfate, and evaporated to give ethyl 4-[3-bromo-4-(hydroxymethyl)phenyl]-7-ethyl-2-methylpyrrolo[1,2-b]pyridazine-3-carboxylate as an yellow oil (54.2 mg).

Workup

  1. additionadditional solution of the borane-tetrahydrofuran complex (0.348 mL) was added
  2. stirringThe mixture was stirred for 15 hours at room temperature
  3. customThe mixture was partitioned between ethyl acetate and 1 N hydrochloric acid
  4. washThe organic layer was washed with water, saturated sodium bicarbonate, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-87b436dc34b34a87923bb22065e50fb4
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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