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Tetrahydrofuran → 3-(5-Bromo-pyridin-3-yl)-quinoline

HRID 383201
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HRID 383201 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)O1.C([O-])([O-])=O.[K+].[K+].C1COCC1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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.C1(C)C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:3]=[N:4][CH:5]=1
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참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 693693,5-DibromopyridineHCID 108485903-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

생성물 1

HCID 120122403-(5-Bromo-pyridin-3-yl)-quinoline수율 98.4%

시약·촉매·용매 4

HCID 74236
Tetrabutylammonium Bromide
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 962Water용매
HCID 1140Toluene용매

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온도
100 °C

실험 절차

1.11 g (4.7 mmol) of 3,5-dibromo-pyridin, 1.0 g (3.92 mmol) of 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline, 0.45 g of tetrakis(triphenylphosphine)palladium(0), 7.84 ml of 2 M K2CO3 and 1.26 g of tetrabutylammoniumbromide were added to a 100 ml round-bottom flask in an argon atmosphere, and 30 ml of THF and 15 ml of toluene were added thereto. Then, the mixture was refluxed at 100° C. for 16 hours. When the mixture solution turned dark brown, water was added thereto and the mixture was subject to extraction using chloroform. Then, an organic layer extracted therefrom was dried using anhydrous magnesium sulfate and filtered. A solvent was removed and the resultant was separated using a silica gel column chromatography to obtain 1.1 g of white solid 3-(5-bromo-pyridin-3-yl)-quinoline which was identified by an atmospheric pressure chemical ionization (APCI) using LCMS (SHIMADZU, LCMS-IT-TOF). As a result, a main peak was observed at [M+H]+=285.

후처리

  1. additionwere added
  2. extractionthe mixture was subject to extraction
  3. extractionThen, an organic layer extracted
  4. customtherefrom was dried
  5. filtrationfiltered
  6. customA solvent was removed
  7. customthe resultant was separated

출처 및 근거

ORD 기록
ord-2635f6812400482c9075355675e53c37
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367219B2

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