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Cesium carbonate → methyl 2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate

HRID 1498243
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HRID 1498243 반응식
I[C:2]1[N:3]=[C:4]2[C:10]3[CH:11]=[CH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:9]=3[O:8][CH2:7][CH2:6][N:5]2[CH:19]=1.[CH:20]([N:23]1[CH:27]=[N:26][CH:25]=[N:24]1)([CH3:22])[CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[NH4+].O>[Cu]I.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O.CN(C=O)C>[CH:20]([N:23]1[C:27]([C:2]2[N:3]=[C:4]3[C:10]4[CH:11]=[CH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:9]=4[O:8][CH2:7][CH2:6][N:5]3[CH:19]=2)=[N:26][CH:25]=[N:24]1)([CH3:22])[CH3:21]
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참가 물질

9

반응물 4

HCID 10796Cesium carbonateHCID 127624431-(propan-2-yl)-1H-1,2,4-triazoleHCID 58204516Methyl 2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxylateHCID 86589665Water ammonium hydroxide

생성물 1

HCID 58204510methyl 2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate수율 28.3%

시약·촉매·용매

4
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To methyl 2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate (1.0 g, 2.7 mmol), 1-isopropyl-1H-1,2,4-triazole (0.30 g, 2.7 mmol), CuI (1.5 g, 8.1 mmol), Pd(OAc)2 (0.061 g, 0.27 mmol), and cesium carbonate (2.2 g, 6.8 mmol) was added DMF (26 mL). The reaction mixture was allowed to stir and heat at 100° C. for 24 hours in a sealed vial. The reaction mixture was cooled to room temperature and poured into a mixture of ammonium hydroxide/water (1:2) and EtOAc and filtered through a pad of silica. The layers were separated and the aqueous portion was extracted with EtOAc. The combined organic extracts were washed with ammonium hydroxide (1:2), water, brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with EtOAc to provide 184 (0.270 g, 28%). 1H NMR (400 MHz, DMSO) δ 8.54 (d, J=8.4, 1H), 7.97 (d, J=35.2, 2H), 7.70 (dd, J=8.4, 1.7, 1H), 7.57 (d, J=1.7, 1H), 5.99-5.70 (m, 1H), 4.57 (q, J=5.9, 4H), 3.87 (s, 3H), 1.49 (d, J=6.6, 6H). MS(ESI(+)): m/z 354.1 (M+H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of silica
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with EtOAc
  5. washThe combined organic extracts were washed with ammonium hydroxide (1:2), water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography on silica gel eluting with EtOAc

출처 및 근거

ORD 기록
ord-439745cb5ba94313bb5163161aa09b84
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09198918B2

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