Cesium carbonate → 6-bromo-4-(4-methoxy-benzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one

HRID 527964노트

반응식

HRID 527964 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][C:8](=[O:12])[NH:9][C:10]=2[N:11]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][C:8](=[O:12])[N:9]([CH2:19][C:18]3[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=3)[C:10]=2[N:11]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

생성물 1

HCID 866493756-bromo-4-(4-methoxy-benzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of 6-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (2.0 g; prepared according to WO 01/30782) in DMF (40 mL) was treated with 4-methoxybenzyl chloride (1.18 mL) and Cs2CO3 (8.5 g) and stirred at rt for 2 h. The solvent was evaporated under reduced pressure and the residue was partitioned between EA and water. The org. layer was washed with brine, dried over MgSO4 and evaporated under reduced pressure. The residue was triturated with Hept, affording a beige solid (2.8 g; 92% yield).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between EA and water
  3. washlayer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with Hept
  7. customaffording a beige solid (2.8 g; 92% yield)

출처 및 근거

ORD 기록
ord-44a340ddae3b4fd0a6a253471ce37dbf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346804B2

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