Sodium Carbonate → 4'-Amino-2'-fluoro-5'-nitrobiphenyl-4-carbonitrile

HRID 1424229ノート

反応式

HRID 1424229 の反応式
Br[C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.[Pd+2].ClC1C=C[C-](P(C(C)(C)C)C(C)(C)C)C=1Cl.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[NH2:6][C:5]1[C:4]([N+:10]([O-:12])=[O:11])=[CH:3][C:2]([C:18]2[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=2)=[C:8]([F:9])[CH:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 219119284-Bromo-5-fluoro-2-nitroaniline

生成物 1

HCID 866991314'-Amino-2'-fluoro-5'-nitrobiphenyl-4-carbonitrile収率 93.1%

試薬・触媒・溶媒 2

HCID 178454866HCID 178454866、化合物触媒HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
60 °C

実験手順

A suspension of 4-bromo-5-fluoro-2-nitroaniline (0.8 g, 3.8 mmol), 4-cyanophenylboronic acid (0.58 g, 3.87 mmol) and sodium carbonate (1 g, 9.50 mmol) in THF/water (15 mL/2 mL) was degassed with nitrogen for 10 minutes. To the suspension was added dichloro [1,1′ bis(di-tert-butylphosphino)]ferrocene palladium (II) (80 mg, 0.095 mmol) and the reaction was heated to 60° C. for 18 hours. The reaction was filtered through celite and the filtrate diluted with water and EtOAc. The organic layer was collected and concentrated in vacuo to afford the title compound as a yellow solid (0.91 g, 91%).

後処理

  1. customwas degassed with nitrogen for 10 minutes
  2. filtrationThe reaction was filtered through celite
  3. additionthe filtrate diluted with water and EtOAc
  4. customThe organic layer was collected
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6bab6169b03b4514bb2be06770e1acf8
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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