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18-Crown-6 → 4-Chloro-2-cyclohexyl-1H-pyrrolo[2,3-b]pyridine

HRID 1521957
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HRID 1521957 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8]C(=O)OC(C)(C)C)[C:3]=1[C:16]#[C:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CC(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:17]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:16][C:3]=12
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참가 물질

5

반응물 3

HCID 2855718-Crown-6HCID 23665647Potassium tert-butoxideHCID 131733115Tert-butyl (4-chloro-3-(cyclohexylethynyl)pyridin-2-yl)carbamate

생성물 1

HCID 904126714-Chloro-2-cyclohexyl-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
85 °C

실험 절차

A solution of Example 98A (870 mg, 2.60 mmol) in 20 mL toluene was treated with potassium tert-butoxide (729 mg, 6.50 mmol) and 18-crown-6 (68.7 mg, 0.260 mmol) and the mixture was heated at 65° C. for 6 hours and at 85° C. overnight. The cooled mixture was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate (twice). The combined organic extracts were rinsed with water (once) and brine (twice), dried over magnesium sulfate, filtered, and concentrated. The residue was suspended in diethyl ether and the solids were collected and rinsed with diethyl ether to afford the title compound. MS (DCI) m/e 235/237 (M+H)+.

후처리

  1. customThe cooled mixture was partitioned between ethyl acetate and water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (twice)
  4. washThe combined organic extracts were rinsed with water (once) and brine (twice),
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe solids were collected
  9. washrinsed with diethyl ether

출처 및 근거

ORD 기록
ord-4aa94d19f7e94ac5bf3b63b532a6172f
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073922B2

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