Dichloromethane → 4-(6-(Fluoromethyl)pyridin-2-yl)but-3-yn-1-amine

HRID 422435Notes

Reaction equation

O.NN.[F:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]#[C:13][CH2:14][CH2:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH:9]=[CH:8][CH:7]=1.C(Cl)Cl>CCO>[F:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]#[C:13][CH2:14][CH2:15][NH2:16])[CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Hydrazine hydrate (1.0 mL, 5.2 mmol) was added to a solution of 2-(4(6-(fluoromethyl)pyridin-2-yl)but-3-ynyl)isoindoline-1,3-dione (320 mg, 1.04 mmol) in EtOH (3 mL) and the reaction mixture was stirred for 4 hours at 50° C. The mixture was cooled down, DCM was added and the aqueous phase was extracted. The organic phase was washed with saturated solution of NaHCO3, dried over Na2SO4; filtered and concentrated to yield 117 mg (0.66 mmol, 630%) of 4(6-(fluoromethyl)pyridin-2-yl)but-3-yn-1-amine as a white solid.

Workup

temperatureThe mixture was cooled down
extractionthe aqueous phase was extracted
washThe organic phase was washed with saturated solution of NaHCO3
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-2ec3877632e14eb790cc32c550b46240
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101637B2

Reaction notes

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