Dichloromethane → 4'-Amino-3-fluoro-3'-nitro-[1,1'-biphenyl]-4-carbonitrile

HRID 1424224ノート

反応式

HRID 1424224 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][C:15]=1[F:23])#[N:13].C(=O)([O-])[O-].[Na+].[Na+].ClCCl>O.O1CCCC1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[C:15]([F:23])[CH:16]=2)=[CH:3][C:4]=1[N+:9]([O-:11])=[O:10]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 701324-Bromo-2-nitroanilineHCID 2783130(4-Cyano-3-fluorophenyl)boronic acid

生成物 1

HCID 866991344'-Amino-3-fluoro-3'-nitro-[1,1'-biphenyl]-4-carbonitrile収率 65%

試薬・触媒・溶媒 3

HCID 178477754HCID 178477754、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

A mixture of 4-bromo-2-nitroaniline (5.02 g, 23.1 mmol), 4-cyano-3-fluorophenylboronic acid (3.62 g, 21.9 mmol), and sodium carbonate (6.1 g, 58 mmol) in water (10 mL) and tetrahydrofuran (35 mL) was sparged with nitrogen for 10 minutes. To this was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.42 g, 0.51 mmol). The reaction mixture was heated at 65° C. for 6 hours. The mixture was allowed to cool, concentrated in vacuo, diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, water and brine. The organic layer was dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with a 0-100% ethyl acetate/hexanes gradient to afford the title compound (3.64 g, 65%) as a yellow solid.

後処理

  1. customwas sparged with nitrogen for 10 minutes
  2. temperatureto cool
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washwashed with saturated aqueous sodium hydrogen carbonate, water and brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. washeluting with a 0-100% ethyl acetate/hexanes gradient

出典と根拠

ORDレコード
ord-5b15dbf40c674c86aac29780f14131ec
出典データセット
uspto-grants-2015_01
特許番号
US08927587B2

反応ノート

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