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

HRID 1916323ノート

反応式

HRID 1916323 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a910c2b52e274dddbdd407545a9c9556
出典データセット
uspto-grants-2013_12
特許番号
US08618092B2

反応ノート

読み込み中…