Lithium aluminum hydride → [6-(4-Chloro-benzylamino)-2-fluoro-pyridin-3-yl]-methanol

HRID 1024185Notes

Reaction equation

HRID 1024185 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]([Cl:18])=[CH:14][CH:13]=2)=[N:6][C:5]=1[F:19].[AlH4-].[Li+]>O1CCCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][NH:10][C:7]2[N:6]=[C:5]([F:19])[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 595933356-(4-Chloro-benzylamino)-2-fluoro-nicotinic acid methyl ester

Product 1

HCID 59593272[6-(4-Chloro-benzylamino)-2-fluoro-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-(4-Chloro-benzylamino)-2-fluoro-nicotinic acid methyl ester (62, 2.00 g, 6.79 mmol) in tetrahydrofuran (100.0 mL) was added lithium tetrahydroaluminate (13.6 mL, 1.00 M in Tetrahydrofuran) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. To the reaction was added an excessive amount of NaSO4.10H2O, and then stirred for 1 hour. Filtration, concentration and purification with silica gel column chromatography eluting with 30% ethyl acetate in hexane provided compound 63 (1.0 g, 55.0%).

Workup

  1. stirringstirred for 1 hour
  2. filtrationFiltration, concentration and purification with silica gel column chromatography
  3. washeluting with 30% ethyl acetate in hexane provided compound 63 (1.0 g, 55.0%)

Sources & evidence

ORD record
ord-428c746ab0e547feba0971303fee3d61
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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