Aluminium lithium hydride → HCID 11217626, compound

HRID 1821831Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([C:11](OCC)=[O:12])[NH:8][C:7]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[C:9]([CH2:11][OH:12])[NH:8][C:7]=12

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (preparation described in Reference Example 1) (230 mg, 1.02 mmol) in tetrahydrofuran (4 mL) at 0° C. under an atmosphere of nitrogen was added portionwise lithium aluminum hydride (94 mg, 2.0 mmol). The reaction mixture was maintained at 0° C. for 4 h then quenched by adding water (100 μL), 15% aqueous sodium hydroxide (100 μL), and water (250 μL) successively. The mixture was filtered through a pad of diatomaceous earth, washing well with ethyl acetate. Solvent evaporation provided 184 mg of crude yellow solid. Purification by column chromatography (silica gel, 60:40 hexanes/ethyl acetate) afforded (7-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)methanol (157 mg, 0.860 mmol, 84%) as an off-white powder: Rf 0.30 (silica gel, 70:30 hexanes/ethyl acetate); mp 185-187° C.; 1H NMR (300 MHz, CD3OD) δ4.94 (2H, s), 6.56 (1H, s), 7.49 (1H, d, J=5.5 Hz), 7.84 (1H, d, J=5.5 Hz); ESI MS m/z 183 [C8H7ClN2O+H]+; HPLC (H2O/CH3CN 100:0 to 0:100 over 20 min, hold for 10 min, 0.05% TFA added to solvents) 95.4% (AUC), tR=11.1 min.

Workup

customthen quenched
additionby adding water (100 μL), 15% aqueous sodium hydroxide (100 μL), and water (250 μL) successively
filtrationThe mixture was filtered through a pad of diatomaceous earth
washwashing well with ethyl acetate
customSolvent evaporation
customprovided 184 mg of crude yellow solid
customPurification by column chromatography (silica gel, 60:40 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-e21e415024b748bd996e44e9437fdebd
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

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