Lithium aluminum hydride → HCID 58368422, compound

HRID 1192569Notes

Reaction equation

HRID 1192569 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([C:12](OC)=[O:13])[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[AlH4-].[Li+]>O1CCCC1>[Br:1][C:2]1[CH:11]=[C:10]([CH2:12][OH:13])[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 67247124HCID 67247124, compound

Product 1

HCID 58368422HCID 58368422, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of methyl 5-bromo-8-(3-fluorophenyl)quinoline-7-carboxylate (0.360 g, 1.00 mmol, from Example 10, Step 4) in tetrahydrofuran (1 mL) was added 1.0 M lithium tetrahydroaluminate in tetrahydrofuran (1.00 mL, 1.00 mmol) at 0° C. The reaction was stirred at room temperature for 30 minutes then quenched by successive addition of 0.038 mL of water, 0.038 mL of 15% NaOH, 0.11 mL of water. After stirred for 30 minutes, the mixture was filtered. The filtrate was dried over magnesium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 80% ethyl acetate in hexane, to give the desired product (150 mg, 45%). LCMS calculated for C16H12BrFNO (M+H)+: m/z=332.0; Found: 332.0.

Workup

  1. customthen quenched by successive addition of 0.038 mL of water, 0.038 mL of 15% NaOH, 0.11 mL of water
  2. stirringAfter stirred for 30 minutes
  3. filtrationthe mixture was filtered
  4. dry with materialThe filtrate was dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-816c7e1482f14cee939a1eaad7e61478
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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