碳酸钾 → (S)-N-(a-ethylbenzyl)-3-(cyanomethoxy)-2-phenylquinoline-4-carboxamide

HRID 651069笔记

反应方程式

HRID 651069 反应方程式
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[OH:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:37][C:38]#[N:39]>C1COCC1>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:37][C:38]#[N:39])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

参与物

5

反应物 3

HCID 11430碳酸钾HCID 11534溴乙腈HCID 5311424TALNETANT

产物 1

HCID 54316707(S)-N-(a-ethylbenzyl)-3-(cyanomethoxy)-2-phenylquinoline-4-carboxamide收率 95.3%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

2.0 g (5.23 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1), 2.21 g of K2CO3, 0.26 g (1.57 mmol) of KI and 0.52 ml (7.85 mmol) of bromoacetonitrile were stirred in 30 ml of dry THF for 5 hours. The inorganic salts were filtered off and the filtrate was evaporated in vacuo to dryness. The residue was dissolved in CH2Cl2 and the organic phase was washed with H2O, sat. sol. NaHCO3, sat. sol. NaCl, separated, dried over Na2SO4 and evaporated in vacuo to dryness to afford 2.10 g of a brown oil which was flash chromatographed on 230-400 mesh silica gel, eluting with a mixture of hexane/EtOAc 70:30. The crude product was triturated with hexane, filtered, washed and dried to yield 0.75 g of the title compound as a white solid.

后处理

  1. filtrationThe inorganic salts were filtered off
  2. customthe filtrate was evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washthe organic phase was washed with H2O, sat. sol. NaHCO3, sat. sol. NaCl
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo to dryness

来源与证据

ORD记录
ord-95dae2f82a1d413f88ba57f8d055dba3
来源数据集
uspto-grants-2001_08
专利号
US06277862B1

反应笔记

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