Dimethylformamide → HCID 66893958、化合物

HRID 1161983ノート

反応式

HRID 1161983 の反応式
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)CCC.CN(C=O)C.[OH-].[Na+]>[Cu]I.C(Cl)(Cl)Cl>[N+:11]([C:4]1[CH:3]=[C:2]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1)([O-:13])=[O:12]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 218647647-Iodo-5-nitrobenzofuran

生成物 1

HCID 66893958HCID 66893958、化合物

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6212Chloroform溶媒

反応条件

温度
100 °C

実験手順

7-Iodo-5-nitrobenzofuran (2.00 g, 0.00692 mol), 4-tributylstannylpyridine (2.80 g, 0.00761 mol), copper(I)iodide (132 mg, 0.692 mmol) and dichlorobis(triphenylphosphine) palladium(II) (49 mg, 0.0692 mmol) were added to a 50 mL test tube followed by DMF (20 mL). The mixture was heated at 100° C. overnight in a StemBlock. After cooling to room temperature, aqueous sodium hydroxide (2 M; 4 mL) was added and the solution was stirred for 15 min. Chloroform (20 mL) was added and the mixture was filtered through Celite. The aqueous layer was then extracted with chloroform (3×) and the combined organic phases were evaporated. The residue was then triturated with ether and the precipitate was dried in vacuo overnight to yield a light brown solid. Yield: 686 mg (41%); HLPC (System A) purity=99%, m/z=241 (M+H)+, 1H NMR (270 MHz, DMSO-d6) δ ppm 7.33 (d, J=2.23 Hz, 1H) 7.98 (m, 2H) 8.38 (d, J=2.23 Hz, 1H) 8.50 (d, J=2.47 Hz, 1H) 8.75 (d, J=2.23 Hz, 1H) 8.79 (m, 2H).

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through Celite
  3. extractionThe aqueous layer was then extracted with chloroform (3×)
  4. customthe combined organic phases were evaporated
  5. customThe residue was then triturated with ether
  6. customthe precipitate was dried in vacuo overnight
  7. customto yield a light brown solid

出典と根拠

ORDレコード
ord-8dec0152ce674285a4af812e86495b03
出典データセット
uspto-grants-2010_10
特許番号
US07820675B2

反応ノート

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