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

HRID 1521957
ノート
印刷プレビュー

反応式

HRID 1521957 の反応式
[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
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

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4aa94d19f7e94ac5bf3b63b532a6172f
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09073922B2

反応ノート

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