POTASSIUM DIPHOSPHATE → methyl 4-(8-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}quinolin-4-yl)benzoate

HRID 38464

反应方程式

HRID 38464 反应方程式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].FC(F)(F)S(O[C:15]1[C:24]2[C:19](=[C:20]([CH:25]3[CH2:27][CH2:26]3)[CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([C:28]([N:30]2[CH2:35][CH2:34][C:33]3([CH2:44][C:43](=[O:45])[C:42]4[C:37](=[CH:38][CH:39]=[C:40]([C:46]5[CH:47]=[N:48][N:49]([CH3:51])[CH:50]=5)[CH:41]=4)[O:36]3)[CH2:32][CH2:31]2)=[O:29])[CH:16]=1)(=O)=O.[CH3:54][O:55][C:56]([C:58]1[CH:63]=[CH:62][C:61](B(O)O)=[CH:60][CH:59]=1)=[O:57]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CC#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:25]1([C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:19]=2[N:18]=[C:17]([C:28]([N:30]2[CH2:35][CH2:34][C:33]4([CH2:44][C:43](=[O:45])[C:42]5[C:37](=[CH:38][CH:39]=[C:40]([C:46]6[CH:47]=[N:48][N:49]([CH3:51])[CH:50]=6)[CH:41]=5)[O:36]4)[CH2:32][CH2:31]2)=[O:29])[CH:16]=[C:15]3[C:61]2[CH:62]=[CH:63][C:58]([C:56]([O:55][CH3:54])=[O:57])=[CH:59][CH:60]=2)[CH2:26][CH2:27]1

参与物

7

反应物 3

HCID 62657POTASSIUM DIPHOSPHATEHCID 27343694-甲氧羰基苯硼酸HCID 582086748-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}quinolin-4-yl trifluoromethanesulfonate

产物 1

HCID 58208703methyl 4-(8-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4'-piperidin]-1'-yl]carbonyl}quinolin-4-yl)benzoate

试剂、催化剂与溶剂 3

HCID 74236四丁基溴化铵催化剂HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)催化剂HCID 6342乙腈溶剂

反应条件

温度
90 °C

实验过程

K3PO4 (109 mg, 0.515 mmol) was added to a stirred mixture of TBAB (8.30 mg, 0.0260 mmol), PdCl2(dppf) (18.9 mg, 0.0260 mmol), 8-cyclopropyl-2-{[6-(1-methyl-1H-pyrazol-4-yl)-4-oxospiro[chroman-2,4′-piperidin]-1′-yl]carbonyl}quinolin-4-yl trifluoromethanesulfonate (165 mg, 0.258 mmol) and [4-(methoxycarbonyl)phenyl]boronic acid (55.6 mg, 0.309 mmol) in MeCN (2 ml) and the mixture was stirred at 90° C. overnight. The mixture was filtered, washing with CHCl3 and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (hexane/EtOAc) to give intended compound as a yellow solid.

后处理

  1. filtrationThe mixture was filtered
  2. washwashing with CHCl3
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silicagel column chromatography (hexane/EtOAc)
  5. customto give

来源与证据

ORD记录
ord-db8cf70bebfe4a1e9f524a59f6376d5c
来源数据集
uspto-grants-2013_09
专利号
US08524730B2

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