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

HRID 1640549
ノート
印刷プレビュー

反応式

HRID 1640549 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]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17]Cl.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]([CH2:17][C:16]3[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=3[O:14][CH3:13])[C:10]=2[N:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 185052611-(Chloromethyl)-2,4-dimethoxybenzeneHCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

生成物 1

HCID 866420676-bromo-4-(2,4-dimethoxy-benzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A suspension of 6-bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (0.412 g, 1.8 mmol) and 2,4-dimethoxybenzyl chloride (0.336 g, 1.8 mmol; freshly prepared according to U.S. Pat. No. 5,817,653) in DMF (5 mL) was treated with Cs2CO3 (1.76 g, 3 eq.). The mixture was stirred at rt for 2 h, partitioned between EA and water. The aq. phase was extracted with EA and the combined org. layers washed with water, and brine, dried over MgSO4 and concentrated. The residue was purified by FC (Hept/EA 1:1) to give the title intermediate as a colourless oil (0.61 g, 90% yield).

後処理

  1. customfreshly prepared
  2. custompartitioned between EA and water
  3. extractionThe aq. phase was extracted with EA
  4. washlayers washed with water, and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by FC (Hept/EA 1:1)

出典と根拠

ORDレコード
ord-9693bf2b05ea497a970b91d225c64443
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08114867B2

反応ノート

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