Dimethylformamide → HCID 22248286, compound

HRID 914906Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[C:23]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:22][CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1)=[O:10].[OH-].[Na+].C(OCC)(=O)C.[CH3:37][N:38](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]([O:24][C:23]1[C:18]([CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([C:9](=[O:10])[CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[C:37]#[N:38])[CH2:12][CH2:13]2)=[N:19][CH:20]=[CH:21][N:22]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 100 °C

Procedure

After dissolving 298 mg of 2-(2-bromophenyl)-1-[1-(3-tert-butoxy-2-pyrazinylmethyl)piperidin-4-yl]ethanone in 2 ml of N,N-dimethylformamide, 235 mg of zinc cyanide and 77 mg of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred overnight at 100° C. A 1N sodium hydroxide solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (90 mg, 34% yield).

Workup

additionwere added
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-771e1418c6f44660954ba53aa64fe6c4
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265108B2

Reaction notes

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