(Diethylamino)sulfur trifluoride → 2-(1-Fluoro-4-(pyridin-2-yl)but-3-ynyl)quinoxaline

HRID 1189224Notes

Reaction equation

CCN(S(F)(F)[F:7])CC.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]#[C:17][CH2:18][CH:19]([C:21]1[CH:30]=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1)O>C(Cl)Cl>[F:7][CH:19]([C:21]1[CH:30]=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1)[CH2:18][C:17]#[C:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=1

Participants

Conditions

Temperature: -78 °C

Procedure

DAST (19 μL, 0.15 mmol) was added dropwise to a solution of 4-pyridin-2-yl-1-quinoxalin-2-yl-but-3-yn-1-ol (30 mg, 0.11 mmol) in DCM (1.5 mL) at −78° C. The reaction mixture was stirred for 15 min. at −78° C., quenched by the addition of water at 0° C. and extracted twice with DCM. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 1:1) to yield 10 mg (36 μmol, 33%) of 2-(1-fluoro-4-(pyridin-2-yl)but-3-ynyl)quinoxaline as an orange semi-solid with a purity of 70%.

Workup

customquenched by the addition of water at 0° C.
extractionextracted twice with DCM
washThe organic phase was washed with water
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customThe crude residue was purified by flash chromatography (cyclohexane/AcOEt 1:1)

Sources & evidence

ORD record: ord-613907fde4a24c16be695aea60ca2c1a
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674106B2

Reaction notes

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