Dimethylformamide → Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylate

HRID 2368380노트

반응식

HRID 2368380 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[C:12]([O:16][C:17]([N:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:20]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23](Br)=[CH:24][N:25]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>[Cu]Br.C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.O>[C:12]([O:16][C:17]([N:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:20]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23]([N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:24][N:25]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 86660188Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate

생성물 1

HCID 70098560Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylate수율 75.5%

시약·촉매·용매 3

HCID 11762Binol촉매HCID 24593copper(I) bromide촉매HCID 962Water용매

실험 절차

A pre-dried flask was charged with copper(I) bromide (0.35 mg, 2.89 μmol), (R)-(+)-1,1′-bi-2-naphthol (1.66 mg, 5.78 μmol) and cesium carbonate (113 mg, 347 μmol) under argon atmosphere. DMF (0.5 ml), methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate (50 mg, 116 μmol) and pyrrolidine (14.3 μl, 174 μmol) were added and the reaction mixture was stirred at r.t. for 1.5 h. The reaction mixture was poured into water (10 ml) and extracted with ethyl acetate. The combined organic layer was washed with brine, dried, evaporated and purified by silica gel chromatography using a heptane/ethyl acetate gradient to yield the product as yellow solid (37 mg, 68%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. customevaporated
  5. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-55ff57ab65c247099b26c316f681399e
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703768B2

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