Pyridine → N-[3-Bromo-6-(methyloxy)-2-pyridinyl]-2,2-dimethyl-N-[(2-oxo-1,3-dioxolan-4-yl)methyl]propanamide

HRID 1943133ノート

反応式

HRID 1943133 の反応式
[Br:1][C:2]1[C:3]([N:10]([CH2:17][CH:18]([OH:21])[CH2:19][OH:20])[C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.N1C=CC=CC=1.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([N:10]([CH2:17][CH:18]2[CH2:19][O:20][C:29](=[O:31])[O:21]2)[C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 68597756N-[3-bromo-6-(methyloxy)-2-pyridinyl]-N-(2,3-dihydroxypropyl)-2,2-dimethylpropanamide

生成物 1

HCID 68597433N-[3-Bromo-6-(methyloxy)-2-pyridinyl]-2,2-dimethyl-N-[(2-oxo-1,3-dioxolan-4-yl)methyl]propanamide収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of N-[3-bromo-6-(methyloxy)-2-pyridinyl]-N-(2,3-dihydroxypropyl)-2,2-dimethylpropanamide (7.628 g, 21.130 mmol) in DCM (100 ml) and pyridine (3.407 ml, 42.26 mmol) at −78° C. under argon was treated with a solution of triphosgene (6.27 g, 21.130 mmol) in DCM (20 ml) over 5 min and the reaction was then allowed warm to rt and stirred at rt for 30 min. The reaction was then carefully treated with saturated sodium bicarbonate solution (200 ml), extracted with DCM (3×200 ml). The organic extracts were dried (MgSO4), and evaporated and chromatographed (0-50% ethyl acetate:Hexane) to give the product as a white solid (5.722 g, 70%).

後処理

  1. extractionextracted with DCM (3×200 ml)
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. customevaporated
  4. customchromatographed (0-50% ethyl acetate:Hexane)

出典と根拠

ORDレコード
ord-cda57d0585994b8f90180d657abbf0b1
出典データセット
uspto-grants-2013_03
特許番号
US08389524B2

反応ノート

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