Aluminium lithium hydride → (2-Fluoro-5-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine

HRID 706463Notes

Reaction equation

[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:7]([O:20][CH3:21])=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:7]([O:20][CH3:21])=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. stirred solution of 2-fluoro-5-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzonitrile (3.25 g, 11.27 mmol) in tetrahydrofuran (50 mL) was added (in three portions) lithium aluminum hydride (0.86 g, 22.55 mmol). Mild gas evolution was noted upon each addition, and the color of the reaction mixture became olive-green. After 1.5 h, the mixture was quenched by the slow addition of water (1.0 mL), 15% sodium hydroxide solution (1.0 mL), and water (3.0 mL). The resulting off-white suspension was allowed to stir at 0° C. After 15 min, the mixture was filtered through Celite with the aid of ethyl acetate. The filtrate was concentrated to provide 1.91 g (58%) of (2-fluoro-5-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)methanamine as a crude oil.

Workup

additionMild gas evolution was noted upon each addition
customthe mixture was quenched by the slow addition of water (1.0 mL), 15% sodium hydroxide solution (1.0 mL), and water (3.0 mL)
waitAfter 15 min
filtrationthe mixture was filtered through Celite with the aid of ethyl acetate
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-e51fac2697664f6a8d99a94aa47f989d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174986B2

Reaction notes

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