N-bromobutanimide → 3-(5-Bromo-3-chloro-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1639658노트

반응식

HRID 1639658 반응식
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:8]([CH3:22])=[N:9][N:10]2[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:14][C:13]([CH3:21])=[N:12][C:11]=12.[Br:23]N1C(=O)CCC1=O>ClCCl>[Br:23][C:5]1[S:4][C:3]([C:7]2[C:8]([CH3:22])=[N:9][N:10]3[C:15]([CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:14][C:13]([CH3:21])=[N:12][C:11]=23)=[C:2]([Cl:1])[CH:6]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 247588843-(3-Chloro-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

생성물 1

HCID 248987433-(5-Bromo-3-chloro-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Dissolve 3-(3-chloro-thiophene-2-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (1.16 g, 3.5 mmol) in dichloromethane (15 mL) and add N-bromosuccinimide (0.69 g, 3.85 mmol) in one aliquot. Stir 2 h under an inert atmosphere and confirm the reaction is complete using TLC. Dilute the reaction with dichloromethane (50 mL), wash with water (75 mL), brine (50 mL), dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure to give a yellow solid (1.56 g, quantative yield). 1H NMR (400 MHz, DMSO): 7.39 (s, 1H), 6.88 (s, 1H), 3.48-3.44 (m, 1H), 2.45 (s, 3H), 2.39 (s, 3H), 1.80-1.73 (m, 4H), 0.76 (t, J=7.0 Hz, 6H).

후처리

  1. additionDilute
  2. washwash with water (75 mL), brine (50 mL)
  3. dry with materialdry over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give
  7. customa yellow solid (1.56 g, quantative yield)

출처 및 근거

ORD 기록
ord-28e813af100e4390a1a131601b2e85af
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110580B2

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