Pyridine → 2,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide

HRID 40538ノート

反応式

HRID 40538 の反応式
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>ClCCl>[CH3:24][C:23]([CH3:26])([CH3:25])[C:22]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][N:13]=1)=[O:27]

参加物

5

反応物 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 468541905-Phenylethynyl-pyridin-2-ylamine

生成物 1

HCID 715482442,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide収率 43.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(65 mg, 0.33 mmol) 5-Phenylethynyl-pyridin-2-ylamine (Example 1, step 1) was dissolved in dichloromethane (3 ml). Pyridine (52 mg, 53 μl, 0.67 mmol, 2 equiv.) and pivaloyl chloride (48 mg, 50 μl, 0.40 mmol, 1.2 equiv.) were added and the mixture was stirred for 2 hours at room temperature. The reaction mixture was extracted with 1N HCl solution and twice with dichloromethane. The organic extracts were combined, dried over sodium sulfate and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with heptane:dichloromethane 50:50. The desired 2,2-dimethyl-N-(5-phenylethynyl-pyridin-2-yl)-propionamide (40 mg, 43% yield) was obtained as a light yellow solid, MS: m/e=279.3 (M+H+).

後処理

  1. extractionThe reaction mixture was extracted with 1N HCl solution and twice with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by flash chromatography on a silica gel column
  5. washeluting with heptane:dichloromethane 50:50

出典と根拠

ORDレコード
ord-f7268b02a0e74b34b0bacc1c837740c9
出典データセット
uspto-grants-2013_09
特許番号
US08530472B2

反応ノート

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