Pyridine → t-Butyl 2-(4-bromobutyramido)-6-methoxypyridine-4-carboxylate

HRID 1612467노트

반응식

HRID 1612467 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=[C:4]([O:15][CH3:16])[N:3]=1.N1C=CC=CC=1.[Br:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>ClCCl.C(OCC)(=O)C>[Br:23][CH2:24][CH2:25][CH2:26][C:27]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH:5]=[C:4]([O:15][CH3:16])[N:3]=1)=[O:28]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 702254-Bromobutyryl chlorideHCID 22252993t-Butyl 2-amino-6-methoxypyridine-4-carboxylate

생성물 1

HCID 22253030t-Butyl 2-(4-bromobutyramido)-6-methoxypyridine-4-carboxylate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of t-butyl 2-amino-6-methoxypyridine-4-carboxylate (D55) (0.263 g) and pyridine (0.12 mL) in dichloromethane (16 mL) under argon, was added 4-bromobutyryl chloride (0.17 mL) dropwise (syringe). The reaction was stirred at room temp for 2.5 h and then diluted with ethyl acetate. The mixture was washed with citric acid solution (10% aq.) and the aqueous layer was re-extracted with ethyl acetate. The combined extracts were washed with aq. bicarbonate, water and brine, dried (MgSO4) and evaporated to give the title compound (D56) as a pale yellow gum (0.47 g).

후처리

  1. washThe mixture was washed with citric acid solution (10% aq.)
  2. extractionthe aqueous layer was re-extracted with ethyl acetate
  3. washThe combined extracts were washed with aq. bicarbonate, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-d5a506df8e284a1d85144cc549e248a0
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992103B2

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