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

HRID 383203
ノート
印刷プレビュー

反応式

HRID 383203 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 74236
Tetrabutylammonium Bromide
触媒
HCID 178418397HCID 178418397、化合物触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-abc8b06cfe5c4a7aa2d98e0b2bc37d7c
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367220B2

反応ノート

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