Methyl iodide → tert-Butyl (2-chloro-3-methylpyridin-4-yl)carbamate

HRID 551282

反応式

HRID 551282 の反応式
[C:1]([Li])(C)(C)C.[C:6]([O:10][C:11](=[O:20])[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)([CH3:9])([CH3:8])[CH3:7].CI>C1COCC1>[C:6]([O:10][C:11](=[O:20])[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[C:14]=1[CH3:1])([CH3:9])([CH3:7])[CH3:8]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 21858447tert-butyl N-(2-chloropyridin-4-yl)carbamateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 70701091tert-Butyl (2-chloro-3-methylpyridin-4-yl)carbamate収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

tert-Butyllithium (29 mL of 1.7M in pentane, 50 mmol) was added dropwise to a vigorously stirring solution of (2-chloropyridin-4-yl)carbamic acid tert-butyl ester (4.57 g, 20 mmol) in THF (150 mL) at −78° C. under nitrogen. The reaction mixture was kept at this temperature for 4 hours before adding a solution of methyl iodide (3.41 g, 24 mmol) in THF (20 mL). Warmed the reaction mixture to 0° C. over 2 hours, and quenched the reaction with saturated aqueous ammonium chloride solution (100 mL). Extracted into ethyl acetate, washed with brine, dried over magnesium sulfate, and concentrated to dryness. Flash column chromatography on silica gel gave the product as a white solid (2.93 g, 12 mmol). 1H NMR (CDCl3) δ 8.11 (d, 1H), 7.98 (d, 1H), 6.58 (br s, 1H), 2.30 (s, 3H), 1.52 (s, 9H). ESI MS (M+1)+: 243, 245 (Cl).

後処理

  1. customquenched
  2. customthe reaction with saturated aqueous ammonium chloride solution (100 mL)
  3. extractionExtracted into ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-77e873a74d9c42d9996d0f4840bf29c3
出典データセット
uspto-grants-2011_05
特許番号
US07947684B2

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