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HCID 21877263, 화합물 → HCID 21877604, 화합물

HRID 724371
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인쇄 미리보기

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HRID 724371 반응식
[CH:1](/[C:9]1[C:17]2[CH2:16][CH2:15][C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][C:12]=2[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1C2C(=CC=CC=2)CCC1.[Pd]>[CH:1](/[C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 1

HCID 21877263HCID 21877263, 화합물

생성물 1

HCID 21877604HCID 21877604, 화합물수율 55%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8404Tetralin용매

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온도
155 °C

실험 절차

A suspension of 3-(E-styryl)-6-phenoxy-4,5-dihydro-1H-indazole (200 mg. 0.64 mmol) and 5% Pd/C (200 mg) in 10 mL of tetralin was heated at 155° C. for 18 h. The catalyst was removed by filtering the hot solution and washed with THF, EtOAc and MeOH. The filtrate was concentrated under reduced pressure and the residue was chromatographed on silica gel eluting hexanes/EtOAc (2:1) to provide 3-(E-styryl)-6-phenoxy-1H-indazole as an off-white solid (110 mg, 55%). 1H NMR (DMSO-d6) δ 6.96 (s, 2H), 7.10 (d, 2H, J=7.7 Hz), 7.20 (t, 1H, J=7.1 Hz), 7.30 (t, 1H, J=7.1 Hz), 7.44 (m, 6H), 7.71 (d, 2H, J=7.5 Hz), 8.20 (d, 1H, J=9.2 Hz), 12.90 (s, 1H). Anal. Calc. for C21H16N2O.0.1H2O: C, 80.28; H, 5.20; N, 8.92. Found: C, 80.20; H, 5.21; N, 8.93.

후처리

  1. customThe catalyst was removed
  2. filtrationby filtering the hot solution
  3. washwashed with THF, EtOAc and MeOH
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. washeluting hexanes/EtOAc (2:1)

출처 및 근거

ORD 기록
ord-2ae6df201b0045b284e4cad8485250a2
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07141587B2

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