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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
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HRID 1640549 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]=[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9693bf2b05ea497a970b91d225c64443
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08114867B2

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