Aluminium lithium hydride → HCID 67093458, compound

HRID 1661595Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][C:13](O)=[O:14])[C:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)=[C:5]2[CH3:22].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][OH:14])[C:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)=[C:5]2[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

A flask is charged with 3-(5-chloro-3-methyl-2-pyridinyl-indol-1-yl)-propionic acid (0.344 g, 1.09 mmol) and THF (10 mL). The reaction mixture is cooled to 0° C. and LAH (1M in THF, 2.73 mL, 2.73 mmol) is added. After stirring at room temperature for 30 min, the mixture is cooled to 0° C., quenched with aqueous NaHCO3 and extracted with ethyl acetate. The organic layer is dried over sodium sulfate and concentrated in vacuo to give a residue which is purified by silica gel flash chromatography (dichloromethane-methanol, 19:1) to afford 3-(5-chloro-3-methyl-2-pyridinyl-indol-1-yl)-propan-1-ol as a white solid. 1H NMR (400 MHz, MeOD) δ ppm 1.71-1.82 (m, 2H), 2.23 (s, 3H), 3.38 (t, J=6.1 Hz, 2H), 4.18-4.24 (m, 2H), 7.21 (dd, J=8.8, 2.0 Hz, 1H), 7.49 (d, J=8.6 Hz, 1H), 7.57 (d, J=1.8 Hz, 1H), 7.65 (ddd, J=7.9, 5.0, 1.0 Hz, 1H), 7.98 (ddd, J=8.1, 2.0, 1.8 Hz, 1H), 8.65 (dd, J=2.3, 0.8 Hz, 1H), 8.67 (dd, J=5.1, 1.8 Hz, 1H). HRMS (ESI) m/z 301.1108 [(M+H)+ Calcd for C17H18ClN2O: 301.1108].

Workup

temperaturethe mixture is cooled to 0° C.
customquenched with aqueous NaHCO3
extractionextracted with ethyl acetate
dry with materialThe organic layer is dried over sodium sulfate
concentrationconcentrated in vacuo
customto give a residue which
customis purified by silica gel flash chromatography (dichloromethane-methanol, 19:1)

Sources & evidence

ORD record: ord-ff10c1151ba440b08d08fd15b768edc4
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030334B2

Reaction notes

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