Ammonium Chloride → 1-(6-Chloropyridazin-3-yl)-1-(2,6-difluorophenyl)but-3-yn-2-one

HRID 1454964Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:9](=[O:16])[C:10]#[C:11][Si](C)(C)C)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[F:24])[C:9](=[O:16])[C:10]#[CH:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(6-chloropyridazin-3-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one (9.6 g, 26.4 mmol) in THF (200 mL) was added TBAF (32.9 mL, 32.9 mmol) at 0° C. After stirring at 0° C. for 15 min, the reaction was poured into aqueous NH4Cl, and extracted with EtOAc. The combined organic layers were washed with 1N HCl, brine, dried over MgSO4, and concentrated to an oil. The crude product was purified by silica gel chromatography (hexanes/CH2Cl2) to give title compound (10.2 g).

Workup

extractionextracted with EtOAc
washThe combined organic layers were washed with 1N HCl, brine
dry with materialdried over MgSO4
concentrationconcentrated to an oil
customThe crude product was purified by silica gel chromatography (hexanes/CH2Cl2)

Sources & evidence

ORD record: ord-2569b45983884ea38e166400524385bf
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482345B2

Reaction notes

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