Potassium Carbonate → 4'-bromo-3'-methyl-N,N-diphenyl-[1,1'-biphenyl]-4-amine

HRID 1755518

반응식

HRID 1755518 반응식
[C:1]1([N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:23][C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][C:25]=1[CH3:31].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[Br:23][C:24]1[CH:29]=[CH:28][C:27]([C:11]2[CH:12]=[CH:13][C:8]([N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:9][CH:10]=2)=[CH:26][C:25]=1[CH3:31]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 120062,5 DibromotolueneHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 867120494'-bromo-3'-methyl-N,N-diphenyl-[1,1'-biphenyl]-4-amine수율 67%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-diphenylaminophenyl boronic acid (1.25 g, 4.33 mmol), 2,5-dibromotoluene (2.16 g, 8.65 mmol), Pd(PPh3)4 (0.25 g, 0.22 mmol) and K2CO3 (1.38 g, 10 mmol) in dioxane/water (50 mL/9 mL) was degassed and heated at 80° C. for 15 hours. The resulting mixture was mixed with ethyl acetate/brine. The organic phase was dried over Na2SO4, loaded on silica gel, and purified by flash column (hexanes to hexanes/dichloromethane 9:1 to 4:1). The desired fraction was collected and concentrated. After removal of solvent, a white solid (Compound 18) was obtained (1.2 g, in 67% yield).

후처리

  1. customwas degassed
  2. additionThe resulting mixture was mixed with ethyl acetate/brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. custompurified by flash column (hexanes to hexanes/dichloromethane 9:1 to 4:1)
  5. customThe desired fraction was collected
  6. concentrationconcentrated
  7. customAfter removal of solvent

출처 및 근거

ORD 기록
ord-1845db619ac84613b0101efc6c84ec6b
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09172051B2

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