8-Bromo-2-(5-tert-butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene → 2-(5-tert-Butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 84665노트

반응식

HRID 84665 반응식
Br[C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:7]=[C:8]([N:14]4[C:18]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:17][N:16]=[N:15]4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1>CO.[Pd]>[C:19]([C:18]1[N:14]([C:8]2[S:9][C:10]3[CH2:11][CH2:12][O:13][C:4]4[CH:3]=[CH:2][CH:24]=[CH:23][C:5]=4[C:6]=3[N:7]=2)[N:15]=[N:16][CH:17]=1)([CH3:22])([CH3:20])[CH3:21]

참가 물질

4

반응물 1

HCID 579003598-Bromo-2-(5-tert-butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

생성물 1

HCID 532349762-(5-tert-Butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene수율 66.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A suspension of 8-bromo-2-(5-tert-butyl-[1,2,3]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (101 mg, 0.25 mmol) and 10% Pd/C (250 mg) in MeOH (5 mL) was stirred at RT under a hydrogen atmosphere for 16 h. The reaction mixture was flushed with nitrogen, filtered through Celite, washed with ethyl acetate and concentrated in vacuo. The resulting residue was purified by flash chromatography (SiO2, 20% ethyl acetate in cyclohexane) to give 434 as a white solid (54 mg, 66%). LCMS (Method C): RT=13.19 min, [M+H]+=327. 1H NMR (CDCl3): 8.30 (1 H, dd, J=7.9, 1.8 Hz), 7.55 (1H, s), 7.29 (1 H, m), 7.17-7.12 (1 H, m), 7.08 (1 H, dd, J=8.0, 1.4 Hz), 4.43 (2 H, t, J=5.1 Hz), 3.39 (2 H, t, J=5.1 Hz), 1.55 (9 H, s).

후처리

  1. customThe reaction mixture was flushed with nitrogen
  2. filtrationfiltered through Celite
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography (SiO2, 20% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-de90e07471fd4a7882c8e59e8f13349a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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