Hydrochloric Acid → HCID 69311335, compound

HRID 860508Notes

Reaction equation

HRID 860508 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].C(OCC)(=O)C.Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 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 parititioned 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. washThe organic layer was washed with water, saturated sodium bicarbonate, and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f402a461ded74a5c967235e25d696a81
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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