Stannous chloride dihydrate → 5-Bromo-2-morpholinopyridin-3-amine

HRID 1431357Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-])=O)[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.O.O.[Sn](Cl)Cl>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred mixture of 4-(5-bromo-3-nitropyridin-2-yl)morpholine (1.02 g, 3.54 mmol) in EtOAc (30 mL) was added tin(II) chloride dihydrate (4.01 g, 17.77 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 90° C. After 2 h, the reaction was cooled to rt and diluted with ethyl acetate, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was identified as 5-bromo-2-morpholinopyridin-3-amine. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.59 (1H, d, J=2.0 Hz), 7.12 (1H, d, J=2.0 Hz), 5.19 (2H, s), 3.80 (4H, m), 3.02 (4H, m).

Workup

additionUpon complete addition of the reducing agent
temperaturethe reaction was cooled to rt
washwashed with 1M NaOH, water, and brine
dry with materialAfter drying over anhydrous sodium sulfate and filtration
customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-cfd583af70354925b83791187d9f71fb
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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