五水硫代硫酸钠 → 1-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazol-5-yl]-2-methoxymethoxy-ethanone

HRID 32011笔记

反应方程式

HRID 32011 反应方程式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([CH:20]([OH:26])[CH2:21][O:22][CH2:23][O:24][CH3:25])=[CH:11][C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]=2[F:19])=[C:4]([Cl:27])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.CCOCC.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:20](=[O:26])[CH2:21][O:22][CH2:23][O:24][CH3:25])=[CH:11][C:12]3[N:16]([CH3:17])[CH:15]=[N:14][C:13]=3[C:18]=2[F:19])=[C:4]([Cl:27])[CH:3]=1

参与物

8

反应物 4

HCID 61475五水硫代硫酸钠HCID 159087戴斯-马丁氧化剂HCID 516892碳酸氢钠HCID 211141711-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazol-5-yl]-2-methoxymethoxy-ethanol

产物 1

HCID 211141721-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazol-5-yl]-2-methoxymethoxy-ethanone收率 71%

试剂、催化剂与溶剂 3

HCID 3283乙醚溶剂HCID 6344二氯甲烷溶剂HCID 8857乙酸乙酯溶剂

实验过程

A solution of 1-[6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazol-5-yl]-2-methoxymethoxy-ethanol 10i (44 mg, 0.096 mmol) and the Dess-Martin periodinane (49 mg, 0.12 mmol) in CH2Cl2 (1.5 mL) is stirred for 1.5 hours at room temperature. The reaction mixture is diluted with ether (3 mL). Saturated aqueous NaHCO3 (1 mL) containing sodium thiosulfate pentahydrate (74 mg) is added. The resulting mixture is stirred for 10 minutes and diluted with EtOAc. The organic layer is washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo to give a crude material which is purified by flash chromatography (1.5% MeOH in CH2Cl2) to afford the desired product (31 mg, 71%): MS APCI (+) m/z 456, 458 (M+, Br pattern) detected.

后处理

  1. additionis added
  2. washThe organic layer is washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude material which
  7. customis purified by flash chromatography (1.5% MeOH in CH2Cl2)

来源与证据

ORD记录
ord-e9c32509e51d4cc49e566892f3e4e21e
来源数据集
uspto-grants-2008_09
专利号
US07425637B2

反应笔记

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