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1,2-Dibromopropane → Ethyl 6,7-dihydro-5H-pyrazolo[5,1-B][1,3]oxazine-3-carboxylate

HRID 1697460
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HRID 1697460 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:11])[NH:8][NH:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH:20](Br)[CH3:21]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]2[CH2:21][CH2:20][CH2:19][O:11][C:7]=12)=[O:5])[CH3:2]
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참가 물질

5

반응물 3

HCID 65531,2-DibromopropaneHCID 11430Potassium CarbonateHCID 238933Ethyl 2,3-dihydro-3-oxo-1H-pyrazole-4-carboxylate

생성물 1

HCID 52228126Ethyl 6,7-dihydro-5H-pyrazolo[5,1-B][1,3]oxazine-3-carboxylate수율 58.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

3-Oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid ethyl ester (13.2 g, 84.5 mmol), potassium carbonate (50 g, 0.3 mol) and N,N-dimethylformamide (500 mL) were combined in a 250 mL round bottom flask, and the mixture was heated to 130° C. 1,2-Dibromo-propane (10.4 mL, 0.10 mol) was added. After 30 minutes, the mixture was partitioned between DCM and water. The aqueous layer was extracted with DCM and the combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The yellow solid was purified by column chromatography (DCM/MeOH) to afford the ester (9.67 g, 58%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ7.62 (s, 1H), 4.41-4.38 (m, 2H), 4.13 (q, 2H), 4.08 (t, 2H, J=6.03 Hz), 2.21-2.15 (m, 2H), 1.21 (t, 3H, J=7.09 Hz).

후처리

  1. customthe mixture was partitioned between DCM and water
  2. extractionThe aqueous layer was extracted with DCM
  3. washthe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe yellow solid was purified by column chromatography (DCM/MeOH)

출처 및 근거

ORD 기록
ord-834678615d694e158ca0aacc84ef59ae
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163901B2

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