Aluminium lithium hydride → HCID 57963218, compound

HRID 1396148Notes

Reaction equation

HRID 1396148 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[N:6][C:5]=1[F:20].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:20][C:5]1[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=[C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57963167HCID 57963167, compound

Product 1

HCID 57963218HCID 57963218, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-fluoro-6-(4-methoxy-benzylamino)-nicotinic acid methyl ester (43, 70 g, 241 mmol) in 350 mL of tetrahydrofuran, lithium aluminum hydride (362 mL, 1 M in tetrahydrofuran, 362 mmol) is added dropwise while cooling. The reaction is stirred at room temperature for 2 hours, then quenched with dropwise addition of 14 mL of water, 14 mL of 15% aqueous sodium hydroxide, and 42 mL of water, sequentially. Then 500 mL of methyl tert-butyl ether is added and solids are removed by filtration. The filtrate is concentrated under vacuum and the resulting solid is dissolved in dichloromethane, passed through a plug of silica gel and eluted with 50-100% ethyl acetate in heptane. The solvent is removed under vacuum to provide the desired compound as an off-white solid (44, 63 g, 240 mmol, 100% yield).

Workup

  1. temperaturewhile cooling
  2. customquenched with dropwise addition of 14 mL of water, 14 mL of 15% aqueous sodium hydroxide, and 42 mL of water
  3. additionThen 500 mL of methyl tert-butyl ether is added
  4. customsolids are removed by filtration
  5. concentrationThe filtrate is concentrated under vacuum
  6. dissolutionthe resulting solid is dissolved in dichloromethane
  7. washeluted with 50-100% ethyl acetate in heptane
  8. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-81cfdbe231a24833a1f0f19a40709a9d
Source dataset
uspto-grants-2014_12
Patent number
US08901118B2

Reaction notes

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