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 2039431ノート

反応式

HRID 2039431 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 58401078Dicyclohexyl(2',6'-dimethoxybiphenyl-3-yl)phosphine触媒HCID 7237O-Xylene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-77d901fe3c9541b3b6d2a277e1de80e0
出典データセット
uspto-grants-2013_11
特許番号
US08580399B2

反応ノート

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