Trimethylsilylacetylene → 3-Nitro-5-((trimethylsilyl)ethynyl)pyridine

HRID 2271653

반응식

HRID 2271653 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:11]([Si:13]([CH3:16])([CH3:15])[CH3:14])#[CH:12]>C(N(CC)CC)C.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.[Cu](I)I>[N+:8]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:12]#[C:11][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1)([O-:10])=[O:9]

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 27628983-Bromo-5-nitropyridine

생성물 1

HCID 667157023-Nitro-5-((trimethylsilyl)ethynyl)pyridine수율 159.3%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

반응 조건

온도
80 °C

실험 절차

To a suspension of 3-bromo-5-nitropyridine (1.0 g, 4.90 mmol), Pd(Ph3P)4 (0.57 g, 0.49 mmol), and copper iodide (0.19 g, 0.98 mmol) in triethylamine (30 mL) was added ethynyltrimethylsilane (1.0 mL, 7.35 mmol) and the reaction was purged with N2. The mixture was stirred at 80° C. for 2 h. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with saturated solutions of NaHCO3 and NaCl. The organic layer was concentrated to afford the crude product (1.72 g) as a light brown solid: ESI MS m/z 221 [C10H12N2O2Si+H]+.

후처리

  1. customthe reaction was purged with N2
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. washThe filtrate was washed with saturated solutions of NaHCO3 and NaCl
  5. concentrationThe organic layer was concentrated

출처 및 근거

ORD 기록
ord-ca7f18693e3641b992c4d5a3cef535c2
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120749B2

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