Aluminium lithium hydride → HCID 57963218, compound

HRID 1775181Notes

Reaction equation

HRID 1775181 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 (63, 70 g, 241 mmol) in 350 mL of tetrahydrofuran, lithium aluminum hydride (362 mL, 1 M in tetrahydrofuran, 362 mmol) was added dropwise while cooling. The reaction was 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. Methyl tert-butyl ether (500 mL) was added and the solids removed by filtration. The filtrate was concentrated under vacuum and the resulting solid was dissolved in dichloromethane, passed through a plug of silica gel and eluted with 50-100% ethyl acetate in heptane. The solvent was removed under vacuum to provide the desired compound as an off-white solid (64, 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. additionMethyl tert-butyl ether (500 mL) was added
  4. customthe solids removed by filtration
  5. concentrationThe filtrate was concentrated under vacuum
  6. dissolutionthe resulting solid was dissolved in dichloromethane
  7. washeluted with 50-100% ethyl acetate in heptane
  8. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-3c6ed055f46d46f5bef2ccf1afd80e1a
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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