1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 4-{1-[6-(2,4-Difluorophenyl)pyridin-2-yl]-2-oxobut-3-yn-1-yl}-3,5-difluorobenzonitrile

HRID 1360695Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([CH:15]([C:24]2[C:31]([F:32])=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=2[F:33])[C:16](=[O:23])[C:17]#[C:18][Si](C)(C)C)[CH:12]=[CH:11][CH:10]=1.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([CH:15]([C:24]2[C:31]([F:32])=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=2[F:33])[C:16](=[O:23])[C:17]#[CH:18])[CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-[1-[6-(2,4-difluorophenyl)pyridin-2-yl]-2-oxo-4-(trimethylsilyl)but-3-yn-1-yl]-3,5-difluorobenzonitrile (from Step F above, 7.00 g, 15.02 mmol) in THF (200 mL) was added tetrabutylammonium fluoride hydrate (22.5 mL, 1.0 M in THF) at 0° C. After stirring at 0° C. for 10 min, the reaction was diluted with EtOAc (3×), washed with aqueous NH4Cl, H2O, brine, dried over MgSO4 and concentrated. The crude residue was purified using silica gel chromatography (hexanes/methylene chloride) to yield the title compound (5.31 g).

Workup

washwashed with aqueous NH4Cl, H2O, brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude residue was purified

Sources & evidence

ORD record: ord-0a9c3aabea1a4ed4979f318e1fab7f46
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879875B2

Reaction notes

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