Potassium Carbonate → HCID 60069826、化合物

HRID 549267ノート

反応式

HRID 549267 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[C:13]([N:20]1[CH2:26][CH2:25]C[NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[N:23]2[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 65020247-Bromo-1-Chloroisoquinoline

生成物 1

HCID 60069826HCID 60069826、化合物収率 54%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
110 °C

実験手順

To a suspension of 7-bromo-1-chloroisoquinoline (3.14 g, 13 mmol) in DMSO (20 mL) at room temperature was added either carboxylic acid tert-butyl (BOC)piperazine (7.23 g, 38.8 mmol) or BOC-homopiperazine (7.77 g, 38.8 mmol) and then potassium carbonate (5.36 g, 39 mmol). The mixture was heated to 110° C. for 24 h. On cooling, the mixture was poured onto ice/water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with water 50 mL) and brine (50 mL). Before drying over anhydrous sodium sulfate. Removal of solvent under reduced pressure gave crude product. Purification was performed by applying the crude material to a plug of silica in a filter funnel and eluting with heptane/ethyl acetate (2:1) and gave 2.73 g (54%) yellow oil. 1H NMR (CDCl3) δ 8.20-8.22 (m, 1H), 8.13-8.18 (d, J=6 Hz, 1H), 7.65-7-71 (dd, J=12, 3 Hz, 1H), 7.59-7.65 (d, J=12 Hz, 1H), 7.21-7.25 (m, 1H), 3.64-3.73 (m, 4H), 7.27-7.36 (m, 4H), 1.49 (s, 9H); LCMS: 392, 394, 395.

後処理

  1. temperatureOn cooling
  2. additionthe mixture was poured onto ice/water (50 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic phases were washed with water 50 mL) and brine (50 mL)
  5. dry with materialBefore drying over anhydrous sodium sulfate
  6. customRemoval of solvent under reduced pressure
  7. customgave crude product
  8. customPurification
  9. washeluting with heptane/ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-32ce83c4efa44273b273320447a41211
出典データセット
uspto-grants-2011_05
特許番号
US07943639B2

反応ノート

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