1-Ethynyl-3,5-difluorobenzene → tert-Butyl 4-[3-(3,5-difluorophenyl)prop-2-ynylidene]piperidine-1-carboxylate

HRID 1895982Notes

Reaction equation

Br[CH:2]=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[C:16]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1)#[CH:17]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[Cu]I.O>[F:24][C:22]1[CH:23]=[C:18]([C:16]#[C:17][CH:2]=[C:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)[CH:19]=[C:20]([F:25])[CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the Compound 49a (0.110 g, 0.40 mmol), palladium tetrakis(triphenylphosphine) (0.023 g, 0.02 mmol), copper(I) iodide (0.0078 g, 0.04 mmol) and 1-ethynyl-3,5-difluorobenzene (49 μL, 0.4 mmol) and TEA (2.5 mL) was heated for 3 h at 80° C. Afterwards, the reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue (0.062 g.), used in the next step without further purification.

Workup

temperatureAfterwards, the reaction mixture was cooled
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
customdried on Na2SO4
customevaporated to dryness in vacuo
customto afford a residue (0.062 g.)
customused in the next step without further purification

Sources & evidence

ORD record: ord-a6f429a3c06a40d8ab15535825911fc2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518916B2

Reaction notes

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