Ethylamine → 4-(ethylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 2261187Notes

Reaction equation

Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([Si](C(C)C)(C(C)C)C(C)C)[CH:11]=[CH:12][C:3]=12.[CH2:23]([NH2:25])[CH3:24]>COC(O)C>[CH2:23]([NH:25][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12)[CH3:24]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1 g, 2.97 mmol), ethyl amine (70 wt. % solution in water, 8 mL, 100 mmol) in methoxyethanol (4 mL) is heated at 120° C. in a sealed tube. After overnight, the reaction mixture is cooled to room temperature and concentrated. The residue is dissolved in HCl solution (1N, 20 mL) and heated at 50° C. After stirring for 1.5 hours, the reaction mixture is basified with saturated sodium bicarbonate solution to pH=8. The solid is collected by filtration and washed with water, then hexanes, dried to afford the title compound as a solid. 1H NMR 600 MHz (DMSO-d6) δ 11.82 (s, 1H), 9.75 (s, 1H), 9.30 (t, 1H, J=4.8 Hz), 8.19 (s, 1H), 7.19 (t, 1H, J=3.6 Hz), 6.72 (m, 1H), 3.73-3.69 (m, 2H), 1.30 (t, 3H, J=7.2 Hz); MS m/z 190.2 (M+1).

Workup

temperaturethe reaction mixture is cooled to room temperature
concentrationconcentrated
dissolutionThe residue is dissolved in HCl solution (1N, 20 mL)
temperatureheated at 50° C
filtrationThe solid is collected by filtration
washwashed with water
dry with materialhexanes, dried

Sources & evidence

ORD record: ord-71a64ceabbb24dcb89de27057de29b08
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846923B2

Reaction notes

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