5-Chloropyrazinoic acid → tert-Butyl 5-chloropyrazine-2-carboxylate

HRID 719896

反応式

HRID 719896 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.ClC(Cl)(Cl)C(=N)O[C:15]([CH3:18])([CH3:17])[CH3:16].[B-](F)(F)(F)[O+](C)C>O1CCCC1.C1CCCCC1.C(OCC)(=O)C>[C:15]([O:9][C:8]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][N:6]=1)=[O:10])([CH3:18])([CH3:17])[CH3:16]

参加物

7

反応物 3

HCID 4654725-Chloropyrazinoic acidHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 178494437HCID 178494437、化合物

生成物 1

HCID 406083tert-Butyl 5-chloropyrazine-2-carboxylate収率 94%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8078Cyclohexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

A solution of 5-chloro-pyrazine-2-carboxylic acid (10.00 g, 63.07 mmol) in tetrahydrofuran (126 mL) was treated with a solution of tert-butyl 2,2,2-trichloroacetimidate (23 mL, 126.14 mmol) in cyclohexane (126 mL). The reaction was stirred at 25° C. for 5 min and then was treated with boron trifluoride dimethyl etherate (3.2 mL, 25.23 mmol). The resulting reaction mixture was stirred at 25° C. for 16 h and then was diluted with ethyl acetate (200 mL), washed with a saturated aqueous sodium bicarbonate solution (200 mL) and water (200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 65M, Silica, 1/9 ethyl acetate/hexanes) afforded 5-chloro-pyrazine-2-carboxylic acid tert-butyl ester (12.73 g, 94%) as a colorless oil: EI-HRMS m/e calcd for C9H11ClN2O2 (M+) 214.0502, found 214.0510.

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred at 25° C. for 16 h
  3. washwashed with a saturated aqueous sodium bicarbonate solution (200 mL) and water (200 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c030f16544b342f1aeffee6bbc07e88a
出典データセット
uspto-grants-2006_11
特許番号
US07132425B2

関連ノート

読み込み中…