Triethylamine → 4-(4-Nitro-2-(trifluoromethyl)phenylethynyl)pyridine

HRID 1912882

反応式

HRID 1912882 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)#[CH:16].C(N(CC)CC)C>CN(C)C=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:16]#[C:15][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 1361982-Bromo-5-nitrobenzotrifluorideHCID 6428014-Ethynylpyridine

生成物 1

HCID 231552744-(4-Nitro-2-(trifluoromethyl)phenylethynyl)pyridine

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

In 20 mL of dimethylformamide, 1.0 g (3.7 mmol) of 4-bromo-3-(trifluoromethyl)nitrobenzene was dissolved, and 0.502 g (3.7 mmol) of 4-ethynylpyridine, 43 mg (3 mol %) of copper iodide, 78 mg (3 mol %) of dichlorobis(triphenylphosphine)palladium and 2.06 mL (0.56 mmol) of triethylamine were added thereto and the mixture solution was stirred overnight at 50° C. in an argon atmosphere. The reaction solution was partitioned between water and ethyl acetate and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The residue was purified by a silica gel column (n-hexane:ethyl acetate=3:1) to obtain 1.3 g (quantitative) of a target product as an pale yellow oil.

後処理

  1. customThe reaction solution was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with a saturated sodium chloride solution
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by a silica gel column (n-hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-178350c2f3cf4c4ebf09de628cdceeb6
出典データセット
uspto-grants-2013_12
特許番号
US08609656B2

関連ノート

読み込み中…