6-Bromo-2-(diethoxymethyl)-1H-pyrrolo[3,2-c]pyridine → 6-Bromo-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

HRID 2205934Notes

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH:11](OCC)[O:12]CC)[NH:10][C:4]=2[CH:3]=1>C1COCC1.O>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([CH:11]=[O:12])[NH:10][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 6-Bromo-2-(diethoxymethyl)-1H-pyrrolo[3,2-c]pyridine (Preparation 137, 142 mg, 0.47 mmole) in THF (1.4 mL) and water (0.28 mL) was added tosic acid hydrate (134 mg, 0.705 mmole) and the reaction was stirred at 25° C. for 55 minutes. The reaction was partitioned between ethyl acetate (20 mL) and sodium bicarbonate (5 mL). The layers were separated and the aqueous layer again extracted with ethyl acetate (7 mL). The combined organic layers were washed with sodium bicarbonate and brine and concentrated in vacuo to afford the title compound (112 mg). 1H-NMR (CDCl3, 500 MHz): δ 7.37 (s, 1H), 7.62 (t, J=0.95 Hz, 1H), 8.88 (d, J=0.95 Hz, 1H), 9.32 (br s, 1H), 9.93 (s, 1H).

Workup

customThe reaction was partitioned between ethyl acetate (20 mL) and sodium bicarbonate (5 mL)
customThe layers were separated
extractionthe aqueous layer again extracted with ethyl acetate (7 mL)
washThe combined organic layers were washed with sodium bicarbonate and brine
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0f603bcfecbe446b955e6a6be3d6b7cd
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371319B2

Reaction notes

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