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

HRID 2271653

反応式

HRID 2271653 の反応式
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]

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 27628983-Bromo-5-nitropyridine

生成物 1

HCID 667157023-Nitro-5-((trimethylsilyl)ethynyl)pyridine収率 159.3%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
80 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-ca7f18693e3641b992c4d5a3cef535c2
出典データセット
uspto-grants-2015_09
特許番号
US09120749B2

関連ノート

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