Acetic Acid → 2-Bromo-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 1505934Notes

Reaction equation

[BH4-].[Na+].Br.[Br:4][C:5]1[S:13][C:8]2[CH2:9][NH:10][CH2:11][CH2:12][C:7]=2[CH:6]=1.[C:14](O)(=O)[CH3:15]>O1CCCC1>[Br:4][C:5]1[S:13][C:8]2[CH2:9][N:10]([CH2:14][CH3:15])[CH2:11][CH2:12][C:7]=2[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium borohydride (146 mg, 3.85 mmol) was added to cooled (0° C.) a suspension of 2-bromo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine hydrobromide (230 mg, 0.77 mmol) in acetic acid (1.5 mL) and tetrahydrofuran (2.8 mL). On complete addition the mixture was heated to 60° C. for 3 h. The mixture was allowed to cool to ambient temperature then partitioned between ethyl acetate and water. The pH of the aqueous phase was adjusted to 10 by the addition of 3N sodium hydroxide solution and the layers separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate and evaporated to give the title compound as a yellow oil (181 mg, 96%). 1H NMR (DMSO-D6, 300 MHz): 6.93 (s, 1H), 3.50-3.47 (m, 2H), 3.66-2.46 (m, 6H), 1.05 (t, J=7.2 Hz, 3H). LCMS (Method B): RT=1.79 min, M+H+=246/248.

Workup

additionOn complete addition the mixture
temperaturewas heated to 60° C. for 3 h
temperatureto cool to ambient temperature
customthen partitioned between ethyl acetate and water
additionThe pH of the aqueous phase was adjusted to 10 by the addition of 3N sodium hydroxide solution
customthe layers separated
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-81256919031f4df5889a233f5b5ebd5f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216980B2

Reaction notes

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