Sodium Carbonate → 9-(3-(5-(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridin-3-yl)phenyl)-9H-carbazole

HRID 520825노트

반응식

HRID 520825 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([N:15]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:21]4[C:16]3=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:12]=[CH:13][CH:14]=2)O1.Br[C:30]1[CH:31]=[C:32]([C:36]2[N:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:39]3[CH:47]=[CH:48][CH:49]=[CH:50][C:38]=3[N:37]=2)[CH:33]=[N:34][CH:35]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[C:41]1([N:40]2[C:39]3[CH:47]=[CH:48][CH:49]=[CH:50][C:38]=3[N:37]=[C:36]2[C:32]2[CH:31]=[C:30]([C:13]3[CH:12]=[C:11]([N:15]4[C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[C:22]5[C:27]4=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH:10]=[CH:9][CH:14]=3)[CH:35]=[N:34][CH:33]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 230940852-(5-bromopyridine-3-yl)-1-phenyl-1H-benzimidazoleHCID 586908999-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole

생성물 1

HCID 866793109-(3-(5-(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridin-3-yl)phenyl)-9H-carbazole수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

A mixture of compound 1C (3.0 g, 8.15 mmol), compound 1F (2.85 g, 8.15 mmol), tetrakistriphenylphosphine palladium (471 mg, 0.408 mmol), and sodium carbonate (3.09 g, 29.2 mmol) in tetrahydrofuran (THF)/water (50 mL/30 mL) was degassed for about 45 minutes. The mixture then heated to reflux (about 80° C.) overnight under argon. After cooling to RT, the reaction mixture was poured into DCM (300 mL) then washed with saturated sodium bicarbonate (200 mL), water (200 mL), and brine (200 mL). The organic phase was then collected, dried over magnesium sulfate, and loaded onto silica gel. A flash column (gradient of 25% to 40% ethyl acetate in DCM) and precipitation from ethyl acetate/methanol gave 2.34 g of HTH-1; 56% yield, pure by HNMR.

후처리

  1. customwas degassed for about 45 minutes
  2. temperatureThe mixture then heated
  3. temperatureAfter cooling to RT
  4. additionthe reaction mixture was poured into DCM (300 mL)
  5. washthen washed with saturated sodium bicarbonate (200 mL), water (200 mL), and brine (200 mL)
  6. customThe organic phase was then collected
  7. dry with materialdried over magnesium sulfate
  8. customA flash column (gradient of 25% to 40% ethyl acetate in DCM) and precipitation from ethyl acetate/methanol
  9. customgave 2.34 g of HTH-1

출처 및 근거

ORD 기록
ord-5ac94c479fd543a099b62b2a86a06e32
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328094B2

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