Aluminium lithium hydride → [2-Methoxy-6-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine

HRID 1479869Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of nitrile 26I (420 mg, 1.5 mmol) in diethyl ether (30 mL) was added in small amounts to a mixture of LiAlH4 (115 mg, 2 mol eq) in diethyl ether (20 mL) stirred at 0° C. After the addition was completed, the mixture was stirred at room temperature overnight. The excess of LiAlH4 was destroyed at 0° C. by addition of small amount of water (30 mL), the solid formed was filtered off and the organic filtrate was separated, washed with brine (50 mL) and dried over Na2SO4. The organic phase was evaporated under reduced pressure to afford 27I as a pale yellow oil (370 mg, 88% yield). 1HNMR (DMSO, 200 MHz) δ 4.13 (s, 3H), 4.22 (s, 2H), 7.56 (s, 1H), 7.88 (d, 2H, J=7.8), 8.26 (s, 1H), 8.51 (d, 2H, J=8).

Workup

additionAfter the addition
stirringthe mixture was stirred at room temperature overnight
customThe excess of LiAlH4 was destroyed at 0° C. by addition of small amount of water (30 mL)
customthe solid formed
filtrationwas filtered off
customthe organic filtrate was separated
washwashed with brine (50 mL)
dry with materialdried over Na2SO4
customThe organic phase was evaporated under reduced pressure

Sources & evidence

ORD record: ord-9f78cfb78b4742c5a28d05333c7e39a4
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

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