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

HRID 1424229노트

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HRID 1424229 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178454866HCID 178454866, 화합물촉매HCID 21881883Oxolane--water (1/1)용매

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온도
60 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6bab6169b03b4514bb2be06770e1acf8
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927587B2

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