Bis(2-bromoethyl) ether → HCID 59426169, compound

HRID 502285Notes

Reaction equation

HRID 502285 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:15]#[N:16])=[CH:7][N:8]2[CH:11]2[CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][O:20][CH2:21][CH2:22]Br.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:11]1([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([N:1]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[CH:10]=3)[C:6]([C:15]#[N:16])=[CH:7]2)[CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 59425321HCID 59425321, compound

Product 1

HCID 59426169HCID 59426169, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-amino-1-cyclobutyl-3-cyanoindole (4.60 g, 21.8 mmol), bromoethylether (6.07 g, 26.16 mmol), DIEA (10.79 mL, 65.4 mmol) in DMF (100 mL) was stirred at 90° C. overnight and then poured into ice-water (1.0 L). The precipitate was filtered, washed with water, and purified on silica gel (CH2Cl2/EtOAc, 9:1) to provide 1-cyclobutyl-6-morpholin-4-yl-1H-indole-3-carbonitrile (5.24 g, 85%).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. custompurified on silica gel (CH2Cl2/EtOAc, 9:1)

Sources & evidence

ORD record
ord-95189a78970a4737afc31a4ce07d2dbe
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

Loading…