Potassium Carbonate → HCID 67540838, 화합물

HRID 579682

반응식

HRID 579682 반응식
B1C2CCCC1CCC2.[CH2:10]([N:13]1[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=[CH2:12].[Br:26][C:27]1[CH:32]=[C:31](Br)[CH:30]=[C:29]([Br:34])[CH:28]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH:24]1[C:25]2[N:13]([CH2:10][CH2:11][CH2:12][C:31]3[CH:32]=[C:27]([Br:26])[CH:28]=[C:29]([Br:34])[CH:30]=3)[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]=2[CH:21]=[CH:22][CH:23]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 122791,3,5-TribromobenzeneHCID 789669-Borabicyclo(3.3.1)nonaneHCID 30903939-Allylcarbazole

생성물 1

HCID 67540838HCID 67540838, 화합물수율 84%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

9-BBN (0.5 M in THF, 38 mL, 19 mmol) was added dropwise into a solution of 9-allylcarbazole (29) (3.0 g, 14.5 mmol) in THF (10 mL) at 0° C. The mixture was stirred at room temperature for 15 minutes and then at 35° C. for 4 hours before transferring into a mixture of 1,3,5-tribromobenzene (19.5 g, 60.3 mmol), Pd(PPh3)4 (0.84 g, 0.72 mmol), K2CO3 (10.0 g, 72.4 mmol), H2O (15 mL) and THF (15 mL). The reaction mixture was stirred at 90° C. overnight, cooled to room temperature, and then extracted with chloroform. The organic extracts were combined, washed with water and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by column chromatography on silica gel with hexane/methlylene chloride 10:1 to 9:1 (v/v) as the eluent to yield 30 as a white crystals (5.4 g, 84%). 1H NMR (400 MHz, CDCl3, 298 K): 8.11-8.10 (d, 2H), 7.49-7.45 (m, 3H), 7.34-7.32 (m, 2H), 7.26-7.20 (m, 4H), 4.37-4.33 (t, 2H), 2.65-2.60 (d, J=7.6 Hz, 2H), 2.25-2.18 (m, 2H).

후처리

  1. stirringThe reaction mixture was stirred at 90° C. overnight
  2. temperaturecooled to room temperature
  3. extractionextracted with chloroform
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customUpon evaporating off the solvent
  7. customthe crude product was purified by column chromatography on silica gel with hexane/methlylene chloride 10:1 to 9:1 (v/v) as the eluent

출처 및 근거

ORD 기록
ord-a489ba637ca64b18ade5ecc8c60ffec0
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040718B2

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