Water → 5-(2'-Thioxospiro[cyclohexane-1,3'-[3H]indol]-5'-YL)-1-methyl-pyrrole-2-carbonitrile

HRID 1760292

반응식

HRID 1760292 반응식
O=[C:2]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]3[N:20]([CH3:21])[C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)[CH:8]=2)[NH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.O>C1(C)C=CC=CC=1>[S:33]=[C:2]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]3[N:20]([CH3:21])[C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)[CH:8]=2)[NH:3]1

참가 물질

5

반응물 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 219862515-(2'-oxospiro[cyclohexane-1,3'-[3H]indol]-5'-yl)-1-methyl-pyrrole-2-carbonitrile

생성물 1

HCID 99271305-(2'-Thioxospiro[cyclohexane-1,3'-[3H]indol]-5'-YL)-1-methyl-pyrrole-2-carbonitrile수율 90.5%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a solution of 5-(2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-1-methyl-pyrrole-2-carbonitrile (0.55 g, 1.8 mmol, 1 eq) in toluene (50 mL) was added Lawesson's reagent (0.47 g, 1.1 mmol, 0.65 eq) and the reaction was heated to 80° C. for 1 hour. The reaction was cooled to room temperature, poured into water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were combined, washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography on silica gel gave the product as a white solid (0.32 g, 55 %). 1H NMR (d6-DMSO, 500 MHz) δ 1.36-1.99 (m, 10 H), 3.7 (s, 3 H), 6.35 (d, 1 H, J=4.2 Hz), 7.05 (d, 1 H, J=4.2 Hz), 7.16 (d, 1 H, J=7.9 Hz), 7.44 (dd, 1 H, J=1.6, 8.1 Hz), 7.83 (d, 1 H, J=1.6 Hz), 12.75 (s, 1 H). MS (ESI) [M−H]−=320. Anal. calcd. for C19H19N3S: C, 70.99; H, 5.96; N, 13.07. Found: C, 68.69; H, 5.36; N, 12.27.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-d24817a98d454f0d8242626b1986ba07
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06841568B2

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