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Tetrahydrofuran → 4-Amino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile

HRID 2246429
ノート
印刷プレビュー

反応式

HRID 2246429 の反応式
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([C:9]#[N:10])[C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][C:18]=1[C:26]([F:29])([F:28])[F:27])[CH3:15].C(=O)([O-])[O-].[K+].[K+].C1COCC1>C(OCC)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH2:14][CH3:15])=[C:18]([C:26]([F:27])([F:29])[F:28])[CH:19]=2)[N:5]=[C:4]([C:9]#[N:10])[C:3]=1[N+:11]([O-:13])=[O:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 445581844-Ethoxy-3-(trifluoromethyl)benzeneboronic acidHCID 552704134-Amino-6-chloro-3-nitropicolinonitrile

生成物 1

HCID 589381224-Amino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile収率 50.7%

試薬・触媒・溶媒 1

HCID 3283
Diethyl Ether
溶媒

反応条件

温度
150 °C

実験手順

A stirred mixture 4-amino-6-chloro-3-nitro-pyridine-2-carbonitrile (1 g, 5.04 mmol), 4-ethoxy-3-trifluoromethylphenylboronic acid (1.33 g, 6.04 mmol), tetrakis-(triphenylphosphine)palladium(0) (˜500 mg,10 mol %), potassium carbonate (2.09 g, 15.12 mmol) and THF (10 ml) was degassed under a stream of nitrogen before heating in the “Smith” microwave at 150° C. for 10 minutes. The crude mixture was concentrated under reduced pressure to remove THF before partitioning between ethyl acetate and water. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure to give a dark brown oil. Trituration with diethylether gave a light brown solid which was filtered and dried under a stream of air to afford 4-amino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-3-nitro-pyridine-2-carbonitrile (900 mg). 1H NMR (DMSO): δ 8.25-8.1 (m, 3H), 7.63 (s, 1H), 7.44 (d, 2H), 4.27 (q, 2H), 1.38 (t, 3H).

後処理

  1. concentrationThe crude mixture was concentrated under reduced pressure
  2. customto remove THF
  3. custombefore partitioning between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a dark brown oil
  8. filtrationwas filtered
  9. customdried under a stream of air

出典と根拠

ORDレコード
ord-7bbb401473a3477ea254cd62539f84bb
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07687515B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート