تفاعل #1509637

ord-d11f7ddb6227481691366563455368a5

معادلة التفاعل

CC1(C)OB(c2ccc(-c3nc4ccccc4n3-c3ccccc3)cc2)OC1(C)C
Compound 10
CC1(C)OB(c2ccc(-c3nc4ccccc4n3-c3ccccc3)cc2)OC1(C)C
1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole
Brc1ccc(-n2c3ccccc3c3ccccc32)cc1
9-(4-bromophenyl)-9H-carbazole
[F-].[K+]
KF
CCOC(C)=O
ethyl acetate
c1ccc(-n2c(-c3ccc(-c4ccc(-n5c6ccccc6c6ccccc65)cc4)cc3)nc3ccccc32)cc1
Compound 11
المردود 47.0%
c1ccc(-n2c(-c3ccc(-c4ccc(-n5c6ccccc6c6ccccc65)cc4)cc3)nc3ccccc32)cc1
9-(4′-(1-phenyl-1H-benzo[d]imidazol-2-yl)biphenyl-4-yl)-9H-carbazole
المردود 47.0%

المذيبات

ظروف التفاعل

درجة الحرارة
120°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةAfter cooling to r.t.
  2. 2
    ترشيحThe resulting mixture was filtered
  3. 3
    أخرىThe solid was collected
  4. 4
    workup.DISSOLUTIONdissolved in DCM (200 mL)
  5. 5
    ترشيحwhich was filtered
  6. 6
    تركيزconcentrated
  7. 7
    أخرىrecrystallized

الإجراء التجريبي

A mixture of Compound 10 (1.41 g, 3.56 mmol), 9-(4-bromophenyl)-9H-carbazole (1.15 g, 3.56 mmol), Pd(dppf)Cl2 (100 mg, 0.14 mmol) and KF (0.619 g, 10.7 mmol) in anhydrous DMF (20 mL) was heated at 120° C. under argon overnight. After cooling to r.t., ethyl acetate (200 mL) was added and the whole was stirred for 15 min. The resulting mixture was filtered. The solid was collected and dissolved in DCM (200 mL), which was filtered, concentrated and recrystallized to give a white solid (Compound 11) (550 mg).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08927121B2uspto-grants-2015_01