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Trifluoroacetic acid → 3-(4,5-Dibromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 1432715
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HRID 1432715 반응식
[Br:1][C:2]1[S:6][C:5]([C:7]2[N:11]3[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]3=[N:9][C:8]=2[CH3:22])=[C:4]([Cl:23])[CH:3]=1.FC(F)(F)C(O)=O.C1C(=O)N([Br:38])C(=O)C1.[OH-].[Na+]>OS(O)(=O)=O>[Br:38][C:3]1[C:4]([Cl:23])=[C:5]([C:7]2[N:11]3[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]3=[N:9][C:8]=2[CH3:22])[S:6][C:2]=1[Br:1]
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참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 579329223-(5-Bromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

생성물 1

HCID 579330503-(4,5-Dibromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine수율 94%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

To a solution of 3-(5-bromo-3-chloro-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (5.92 g, 14.34 mmol) and trifluoroacetic acid (40 mL) and 98% H2SO4 (10 ml) is added NBS (3.83 g, 21.15 mmol). After 10 minutes the solution is poured into ice, and made basic with 5M NaOH. The slurry is extracted with EtOAc (3×100 mL), the combined organic layers washed with water (2×400 mL), brine (400 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (6.61 g, 13.44 mmol, 94%). 1H NMR (CDCl3) δ 0.87 (t, J=7.5 Hz, 6H), 1.72-1.92 (m, 4H), 2.47 (s, 3H), 2.52 (s, 3H), 3.25-3.34 (m, 1H), 6.72 (s, 1H). LC/MS (m/z): calcd. for C17H18Br2ClN3S (M+H)+: 489.9; found: 490.0.

후처리

  1. additionAfter 10 minutes the solution is poured into ice
  2. extractionThe slurry is extracted with EtOAc (3×100 mL)
  3. washthe combined organic layers washed with water (2×400 mL), brine (400 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-50136b62c9974bb5b1cdde7febe23637
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612067B2

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