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

HRID 2240962

반응식

HRID 2240962 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매

실험 절차

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+·].

후처리

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

출처 및 근거

ORD 기록
ord-b3d943fd09aa4dbabfd02a842d180be4
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723368B2

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