Cesium carbonate → HCID 68412430, compound

HRID 1511667Notes

Reaction equation

HRID 1511667 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([O:10][CH:11]2[CH2:16][NH:15][CH2:14][C:13]3[O:17][CH:18]=[CH:19][C:12]2=3)[CH:6]=[CH:7][C:8]=1[Cl:9].C(=O)([O-])[O-].[Cs+].[Cs+].[C:26]([O:30][C:31]([NH:33][CH2:34][CH2:35]Br)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[C:26]([O:30][C:31]([NH:33][CH2:34][CH2:35][N:15]1[CH2:16][CH:11]([O:10][C:5]2[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=2)[C:12]2[CH:19]=[CH:18][O:17][C:13]=2[CH2:14]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 68410874HCID 68410874, compound

Product 1

HCID 68412430HCID 68412430, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-(3,4-Dichlorophenyloxy)-4,5,6,7-tetrahydrofuro-[2,3-c]pyridine hydrochloride (Example 119) (100 mg) was dissolved in 2 mL of DMF and then 256 mg of cesium carbonate and 87 mg of N-(tert-butoxycarbonyl)-2-bromoethylamine were added successively thereto. This reaction solution was heated at 80° C. with stirring overnight and poured over 30 mL of ice water followed by extracting with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The residue was purified by silica gel column chromatography to give 35 mg of the objective product as an oily substance.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d9644dc8505e4b018f70719ef3be3b4a
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

Loading…