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Potassium Carbonate → 1-(5-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)phenyl)cyclobutanecarbonitrile

HRID 925123
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HRID 925123 반응식
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Br[CH2:27][CH2:28][CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>CC#N>[CH3:9][O:8][C:7]1[C:2]([O:1][CH2:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:3][C:4]([N+:16]([O-:18])=[O:17])=[C:5]([C:10]2([C:14]#[N:15])[CH2:11][CH2:12][CH2:13]2)[CH:6]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 13034045HCID 13034045, 화합물HCID 921351291-(4-Hydroxy-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile

생성물 1

HCID 1183893681-(5-Methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)phenyl)cyclobutanecarbonitrile수율 59.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

To a solution of 1-(4-(hydroxyl)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile (0.73 g, 2.93 mmol), from Step 3, in MeCN (20 mL) was added potassium carbonate (1.215 g, 8.79 mmol) and 1-(3-bromopropyl)pyrrolidine hydrochloride (1 g, 4.4 mmol) and stirred at 100° C. for 3 hours. The reaction mixture was concentrated, and extracted with dichloromethane. The combined organic extracts were washed with brine. The organic layer was dried (MgSO4), filtered and concentrated. Purification by flash chromatography (silica gel, 5-20% methanol/dichloromethane) afforded 0.63 g (59%) of 1-(5-methoxy-2-nitro-4-(3-(pyrrolidin-1-yl)propoxy)phenyl)cyclobutanecarbonitrile. 1H NMR (400 MHz, METHANOL-D4) δ 7.65 (s, 1H), 6.94 (s, 1H), 4.14 (t, J=6.1 Hz, 2H), 3.97 (s, 3H), 2.87 (ddd, J=8.6, 5.3, 2.5 Hz, 2H), 2.77-2.67 (m, 2H), 2.68-2.52 (m, 6H), 2.42 (dd, J=14.6, 6.3 Hz, 1H), 2.13-2.01 (m, 2H), 2.01-1.89 (m, 1H), 1.84 (dt, J=6.6, 3.2 Hz, 4H). MS (ESI) m/z 360 (M+H)+.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with dichloromethane
  3. washThe combined organic extracts were washed with brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, 5-20% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-af3b0ebb00f34e9a8080b48104507b3a
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284272B2

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