Toluene → HCID 86712053, 화합물

HRID 1755525

반응식

HRID 1755525 반응식
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]1[CH:30]=CC=C[C:26]=1C.[CH3:33][C:34]([CH3:37])([O-])[CH3:35].[Na+].[C:39]1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:15][C:8]1[CH:7]=[C:6]2[C:11]([C:12]3[CH:13]=[CH:14][C:2]([N:24]([C:19]4[CH:18]=[CH:23][C:22]([CH3:39])=[CH:21][CH:20]=4)[C:25]4[CH:26]=[CH:35][C:34]([CH3:37])=[CH:33][CH:30]=4)=[CH:3][C:4]=3[C:5]2([CH3:16])[CH3:17])=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 136423Benzenamine, 2-methyl-N-(2-methylphenyl)-HCID 121238762,7-Dibromo-9,9-dimethylfluoreneHCID 23676156Sodium t-butoxide

생성물 1

HCID 86712053HCID 86712053, 화합물수율 66.6%

시약·촉매·용매 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

반응 조건

온도
80 °C

실험 절차

A mixture of 2,7-dibromo-9,9-dimethyl-9H-fluorene (31.64 g, 89.87 mmol), ditolylamine (8.865 g, 44.9 mmol), Pd(dppf)Cl2 (1.644 g, 2.25 mmol) and sodium tert-butoxide (10.796 g, 112.3 mmol) in toluene 400 mL was degassed and heated at about 80° C. overnight. The resulting mixture was poured into ethyl acetate (500 mL). After the precipitate was filtered off, the solution was washed with water and brine, dried over Na2SO4, loaded on silica gel and purified by flash column (hexane to hexanes/dichloromethane 99:1 to 95:5 gradients). After removal of solvent and recrystallization in dichloromethane/hexanes, a white solid (Compound 32) was obtained (14.0169 g, in 66.6% yield).

후처리

  1. customwas degassed
  2. additionThe resulting mixture was poured into ethyl acetate (500 mL)
  3. filtrationAfter the precipitate was filtered off
  4. washthe solution was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. custompurified by flash column (hexane to hexanes/dichloromethane 99:1 to 95:5 gradients)
  7. customAfter removal of solvent and recrystallization in dichloromethane/hexanes

출처 및 근거

ORD 기록
ord-dbcc9cdabf984bc6a8ebafc47ca3c079
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09172051B2

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