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2-Bromopyridine → 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)but-3-yn-1-ol

HRID 546374
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인쇄 미리보기

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HRID 546374 반응식
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:15])[CH2:12][C:13]#[CH:14])([CH3:3])[CH3:2].Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:15])[CH2:12][C:13]#[C:14][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)([CH3:3])[CH3:2]
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참가 물질

6

반응물 2

HCID 79732-BromopyridineHCID 866439371-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol

생성물 1

HCID 671891181-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)but-3-yn-1-ol수율 43.6%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 8471Triethylamine용매

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온도
60 °C

실험 절차

To a round bottom flask were added 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol (0.47 g, 2.3 mmol), triethylamine (10 mL), 2-bromopyridine (0.28 mL, 2.7 mmol), bis(triphenylphosphine)palladium(II) dichloride (16 mg, 0.023 mmol) and copper(I) iodide (9 mg, 0.045 mmol). After this mixture was stirred with heating overnight at 60° C., it was allowed to cool to room temperature. The reaction was mixed directly with silica, concentrated and purified by silica chromatography to give the desired coupling product (286 mg).

후처리

  1. temperatureto cool to room temperature
  2. additionThe reaction was mixed directly with silica
  3. concentrationconcentrated
  4. custompurified by silica chromatography

출처 및 근거

ORD 기록
ord-43f11b5f8d3d4467a492c2351b454c24
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935848B2

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