Pyridine → Benzyl (4-chloropyridin-3-yl)carbamate

HRID 69950

反応式

HRID 69950 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[Cl:19].N1C=CC=CC=1>C1COCC1>[Cl:19][C:18]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[NH:12][C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 5819323-Amino-4-chloropyridine

生成物 1

HCID 69042933Benzyl (4-chloropyridin-3-yl)carbamate収率 34%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of benzyl chloroformate (1.1 equiv.) in THF (1.85 M) was slowly added to a solution of 3-amino-4-chloropyridine (1.0 equiv.) and pyridine (1.5 equiv.) in THF (1.0 M) and stirred at rt for 3.5 hours (formation of a precipitate over time). The reaction was quenched with H2O (100 mL), extracted with EtOAc (200 mL), washed with NaCl(sat.) (75 mL), dried over MgSO4, filtered and the volatiles were removed in vacuo. The product precipitated from a mixture of hexane/EtOAc yielding benzyl 4-chloropyridin-3-ylcarbamate (34%). LCMS (m/z): 263.1 (MH+); LC Rt=2.33 min.

後処理

  1. customThe reaction was quenched with H2O (100 mL)
  2. extractionextracted with EtOAc (200 mL)
  3. washwashed with NaCl(sat.) (75 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe volatiles were removed in vacuo
  7. customThe product precipitated from a mixture of hexane/EtOAc

出典と根拠

ORDレコード
ord-fe4cb553cd4346b4a655937987b025fe
出典データセット
uspto-grants-2014_09
特許番号
US08822497B2

関連ノート

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