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Water → 2-Fluoro-5-nitro-[1,1';4'1'']terphenyl-4-ylamine

HRID 1960130
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HRID 1960130 반응식
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[F:22][C:23]1[C:24](I)=[CH:25][C:26]([N+:30]([O-:32])=[O:31])=[C:27]([NH2:29])[CH:28]=1.O>C1(C)C=CC=CC=1.CN(C=O)C.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:22][C:23]1[CH:28]=[C:27]([NH2:29])[C:26]([N+:30]([O-:32])=[O:31])=[CH:25][C:24]=1[C:13]1[CH:14]=[CH:15][C:10]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:11][CH:12]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 574814875-Fluoro-4-iodo-2-nitrobenzenamine

생성물 1

HCID 674465092-Fluoro-5-nitro-[1,1';4'1'']terphenyl-4-ylamine

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 1140Toluene용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

A mixture of 4-Biphenylboronic acid (737 mg, 2.4 mmol), K2CO3 (995 mg, 7.2 mmol), Pd(PPh3)4 (139 mg, 0.12 mmol), compound 13-1 (700 mg, 2.4 mmol) in 10 mL toluene, 2 mL DMF, and 2 mL H2O was suspended in a microwave reactor vial and heated to 130° C. for 10 min in a microwave reactor. The resulting dark solution was then diluted with EtOAc (150 mL) and washed three times with 50 mL portions of saturated aqueous NH4Cl. The combined organic layers were dried over MgSO4 filtered and concentrated in vacuo. The crude product was purified on ISCO (EtOAc/Hexanes=6/4) to give title compound 13-2.

후처리

  1. customwas suspended in a microwave reactor
  2. washwashed three times with 50 mL portions of saturated aqueous NH4Cl
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified on ISCO (EtOAc/Hexanes=6/4)

출처 및 근거

ORD 기록
ord-6eb49e05e5064b598da627267f7afe8a
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410284B2

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