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 2079035ノート

反応式

HRID 2079035 の反応式
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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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 (1H, dd, J=7.9, 1.8 Hz), 7.55 (1H, s), 7.29 (1H, m), 7.17-7.12 (1H, m), 7.08 (1H, dd, J=8.0, 1.4 Hz), 4.43 (2H, t, J=5.1 Hz), 3.39 (2H, t, J=5.1 Hz), 1.55 (9H, s).

後処理

  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)

出典と根拠

ORDレコード
ord-c2a53da5d6ad4d31b0e1a84e0a062afa
出典データセット
uspto-grants-2011_04
特許番号
US07928248B2

反応ノート

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