Cesium carbonate → Methyl 1-(1-cyclopropyl-6-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}-1H-indol-4-yl)piperidine-4-carboxylate

HRID 38466노트

반응식

HRID 38466 반응식
C([O-])([O-])=O.[Cs+].[Cs+].FC(F)(F)S(O[C:13]1[CH:21]=[C:20]([C:22]([N:24]2[CH2:29][CH2:28][C:27]3([CH2:38][C:37](=[O:39])[C:36]4[C:31](=[CH:32][CH:33]=[C:34]([C:40]5[CH:41]=[N:42][N:43]([CH3:45])[CH:44]=5)[CH:35]=4)[O:30]3)[CH2:26][CH2:25]2)=[O:23])[CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][N:17]2[CH:46]1[CH2:48][CH2:47]1)(=O)=O.[NH:51]1[CH2:56][CH2:55][CH:54]([C:57]([O:59][CH2:60]C)=[O:58])[CH2:53][CH2:52]1.C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:46]1([N:17]2[C:18]3[C:14](=[C:13]([N:51]4[CH2:56][CH2:55][CH:54]([C:57]([O:59][CH3:60])=[O:58])[CH2:53][CH2:52]4)[CH:21]=[C:20]([C:22]([N:24]4[CH2:25][CH2:26][C:27]5([CH2:38][C:37](=[O:39])[C:36]6[C:31](=[CH:32][CH:33]=[C:34]([C:40]7[CH:41]=[N:42][N:43]([CH3:45])[CH:44]=7)[CH:35]=6)[O:30]5)[CH2:28][CH2:29]4)=[O:23])[CH:19]=3)[CH:15]=[CH:16]2)[CH2:47][CH2:48]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 70770Ethyl 4-piperidinecarboxylateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 582087121-cyclopropyl-6-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}-1H-indol-4-yl trifluoromethanesulfonate

생성물 1

HCID 67055541Methyl 1-(1-cyclopropyl-6-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}-1H-indol-4-yl)piperidine-4-carboxylate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

Cs2CO3 (261 mg, 0.800 mmol), Pd(OAc)2 (8.98 mg, 0.040 mmol), 1-cyclopropyl-6-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4′-piperidin]-1′-yl]carbonyl}-1H-indol-4-yl trifluoromethanesulfonate (251 mg, 0.4 mmol), ethyl 4-piperidinecarboxylate (94.0 mg, 0.600 mmol) and biphenyl-2-yl(di-tert-butyl)phosphine (11.9 mg, 0.0400 mmol) were suspended in 1,4-dioxane (3 ml) and the mixture was stirred at 100° C. overnight. The mixture was filtered through celite pad, washing with CHCl3, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (CHCl3/MeOH), then preparative-TLC (CHCl3/MeOH) to give intended compound as brown oil.

후처리

  1. filtrationThe mixture was filtered through celite pad
  2. washwashing with CHCl3
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silicagel column chromatography (CHCl3/MeOH)
  5. custompreparative-TLC (CHCl3/MeOH) to give

출처 및 근거

ORD 기록
ord-2e513f059c534c47bb77afa38ccd88a4
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524730B2

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