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 38466ノート

反応式

HRID 38466 の反応式
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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2e513f059c534c47bb77afa38ccd88a4
出典データセット
uspto-grants-2013_09
特許番号
US08524730B2

反応ノート

読み込み中…