Sodium t-butoxide → 9-(9-(3'-(Dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-carbazol-3-yl)-pyrido[2,3-b]indole

HRID 2039431노트

반응식

HRID 2039431 반응식
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3[CH:23]=[CH:24][CH:25]=[N:26][C:15]2=3)[CH:2]=1.Br[C:28]1[CH:29]=[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]3[C:45]4[S:46][C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=5[C:44]=4[CH:43]=[CH:42][CH:41]=3)[CH:35]=2)[CH:31]=[CH:32][CH:33]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=C(C3C(OC)=CC=CC=3OC)C=CC=2)CCCCC1>[CH:43]1[C:44]2[C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=3[S:46][C:45]=2[C:40]([C:36]2[CH:35]=[C:34]([C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([N:12]4[C:13]5[CH:1]=[CH:2][C:3]([N:14]6[C:22]7[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=7)[C:16]7[CH:23]=[CH:24][CH:25]=[N:26][C:15]6=7)=[CH:4][C:5]=5[C:6]5[C:11]4=[CH:10][CH:9]=[CH:8][CH:7]=5)[CH:29]=3)[CH:39]=[CH:38][CH:37]=2)=[CH:41][CH:42]=1

참가 물질

7

반응물 3

HCID 23676156Sodium t-butoxideHCID 669744624-(3'-Bromobiphenyl-3-yl)dibenzothiopheneHCID 708151019-(9H-carbazol-3-yl)-pyrido[2,3-b]indole

생성물 1

HCID 708151359-(9-(3'-(Dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)-carbazol-3-yl)-pyrido[2,3-b]indole수율 64.1%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 58401078Dicyclohexyl(2',6'-dimethoxybiphenyl-3-yl)phosphine촉매HCID 7237O-Xylene용매

실험 절차

A solution of 9-(9H-carbazol-3-yl)-pyrido[2,3-b]indole (2.50 g, 7.50 mmol), 4-(3′-bromo-[1,1′-biphenyl]-3-yl)dibenzo[b,d]thiophene (3.11 g, 7.50 mmol), Pd2(dba)3 (0.137 g, 0.150 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (0.123 g, 0.30 mmol), and sodium tert-butoxide (1.44 g, 15.00 mmol) in xylene (150 mL) was refluxed in nitrogen overnight. After cooling to room temperature, the reaction mixture was washed with water, dried over Na2SO4 and the solvent was evaporated. The residue was dissolved in hot toluene, mixed with celite, and purified by column chromatography with hexane:toluene (1:9 to 0:10, v/v) as eluent. The product was precipitated in ethanol, and further purified by thermal sublimation under vacuum (<105 torr) to yield 9-(9-(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)-carbazol-3-yl)-pyrido[2,3-b]indole as a white glassy solid (3.21 g).

후처리

  1. washthe reaction mixture was washed with water
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in hot toluene
  5. additionmixed with celite
  6. custompurified by column chromatography with hexane:toluene (1:9 to 0:10
  7. customThe product was precipitated in ethanol
  8. customfurther purified by thermal sublimation under vacuum (<105 torr)

출처 및 근거

ORD 기록
ord-77d901fe3c9541b3b6d2a277e1de80e0
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580399B2

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