Aluminium lithium hydride → 6-chloro-5-fluoro-1H-indol-3-yl-1-methyl-ethylamine

HRID 555338Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](C=C([N+]([O-])=O)C)=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:17].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([NH:8][CH:9]([CH3:10])[CH3:5])=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:17]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6-chloro-5-fluoro-3-(2-nitro-propenyl)-1H-indole (5.0 g, 19.63 mmol) in tetrahydrofuran (10 mL) was added to the suspension of lithium aluminium hydride (2.92 g, 78.54 mmol) in tetrahydrofuran (20 mL) at 0° C. and then refluxed for 3 hours. The reaction mixture was cooled to 0° C., and quenched according to the Fischer method. The reaction mixture was filtered through celite and the filtrate concentrated to give 2-(6-chloro-5-fluoro-1H-indol-3-yl-1-methyl-ethylamine (4.7 g crude) as a viscous brown liquid. The residue was used without further purification. 1H NMR (500 MHz, CDCl3): δ 8.13 (s, 1H), 7.37 (d, 1H, 6.Hz), 7.32 (d, 1H, J=10 Hz), 7.08 (s, 1H), 3.23-3.26 (m, 1H), 2.77-2.81 (m, 1H), 2.58-2.63 (m, 1H), 1.15 (d, 3H, J=6.5 Hz).

Workup

temperaturerefluxed for 3 hours
customquenched
filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate concentrated

Sources & evidence

ORD record: ord-59a534608d2f4427aeb26ab1b4e93d5b
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053442B2

Reaction notes

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