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

HRID 1639658ノート

反応式

HRID 1639658 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-28e813af100e4390a1a131601b2e85af
出典データセット
uspto-grants-2012_02
特許番号
US08110580B2

反応ノート

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