Lithium aluminum hydride → 2-Fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-pyridin-3-yl-methanol

HRID 1024262Notes

Reaction equation

HRID 1024262 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:13]=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=[N:6][C:5]=1[F:22].[AlH4-].[Li+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:22][C:5]1[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=[C:7]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:17]=2)[N:6]=1

Participants

5

Reactant 3

HCID 28112Lithium aluminum hydrideHCID 62649Sodium sulfate decahydrateHCID 576193682-Fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-nicotinic acid methyl ester

Product 1

HCID 576193002-Fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-pyridin-3-yl-methanolYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-fluoro-6-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-nicotinic acid methyl ester (562, 1.40 g, 4.25 mmol) in tetrahydrofuran (100.0 mL) under an atmosphere of nitrogen at room temperature, a solution of lithium tetrahydroaluminate (1.00M in tetrahydrofuran, 10.0 mL) was added slowly. The reaction was stirred at room temperature overnight, followed by addition of an appropriate amount of sodium sulfate decahydrate. After 1 hour, the reaction mixture was filtered and concentrated to give crude compound (563, 1.2 g, 93.7%) that was used in the next step without further purification.

Workup

  1. waitAfter 1 hour
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3932f75a5c264923a227d3276bcd36a8
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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