Sodium borohydride → HCID 69309219, compound

HRID 860438Notes

Reaction equation

HRID 860438 reaction equation
[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH3:27])[C:9]([CH2:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[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.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH3:27])[C:9]([CH2:18][CH:19]([OH:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69308208HCID 69308208, compound

Product 1

HCID 69309219HCID 69309219, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-[7-chloro-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]-3-oxo-butanoate (160 mg) in methanol (5 ml) was added sodium borohydride (23.4 mg) at 0° C. and the mixture was stirred at the same temperature for 1 hour. The mixture was partitioned between 1N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was purified by preparative thin-layer chromatograpy eluting with a mixture of ethyl acetate and hexane (1:3) and triturated with ethyl acetate to give ethyl 4-[7-chloro-4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazin-3-yl]-3-hydroxybutanoate (95 mg) as an yellow powder.

Workup

  1. customThe mixture was partitioned between 1N hydrochloric acid and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by preparative thin-layer chromatograpy
  7. washeluting with a mixture of ethyl acetate and hexane (1:3)
  8. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-3ec3997941af4d86a2a0f6bbd65659bd
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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