Triethylamine → {3-[3-(2-Fluoro-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane

HRID 2240962

Reaction equation

HRID 2240962 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:11][CH:10]([CH2:12][CH2:13][F:14])[CH2:9]2)[CH:3]=1.[CH:15]([Si:18]([C:25]#[CH:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16].C(N(CC)CC)C>[Cu](I)I.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>[F:14][CH2:13][CH2:12][CH:10]1[CH2:11][CH:8]([C:4]2[CH:3]=[C:2]([C:26]#[C:25][Si:18]([CH:15]([CH3:17])[CH3:16])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])[CH:7]=[CH:6][CH:5]=2)[CH2:9]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734682(Triisopropylsilyl)acetyleneHCID 593053661-Bromo-3-[3-(2-fluoro-ethyl)-cyclobutyl]-benzene

Product 1

HCID 59305330{3-[3-(2-Fluoro-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silaneYield 80.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

In a CEM snap top microwave vial were combined 1-Bromo-3-[3-(2-fluoro-ethyl)-cyclobutyl]-benzene (0.250 gm 9.72 mmol), triisopropylsilylacetylene (0.22 gm, 1.21 mmol), copper iodide (7 mg, 0.178 mmol), tetrakis(triphenylphosphine)palladium (22 mg, 0.088 mmol) and triethylamine (0.600 g, 5.93 mmol). The vial was quickly agitated then irradiated in a CEM Explorer™ microwave instrument for 30 minutes at 80° C. Purification by column chromatography (hexanes) afforded an oil 349 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06 (s, 21H) 1.62-1.81 (m, 2H) 1.82-1.97 (m, 1H) 2.00-2.45 (m, 4H) NMR (400 MHz, DMSO-d6) δ ppm 3.31-3.62 (m, 1H) 4.30-4.51 (m, 2H) 7.17-7.41 (m, 4H); MS (EI) m/z 256 [M+·].

Workup

  1. customthen irradiated in a CEM Explorer™ microwave instrument for 30 minutes at 80° C
  2. customPurification by column chromatography (hexanes)

Sources & evidence

ORD record
ord-b3d943fd09aa4dbabfd02a842d180be4
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Linked notes

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