Butyl bromide → HCID 68609508, compound

HRID 1991107Notes

Reaction equation

HRID 1991107 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([OH:16])[CH:14]=3)[N:9]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:8]=2)[CH:4]=[N:3]1.Br[CH2:26][CH2:27][CH2:28][CH3:29].C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CC(C)=O>[CH2:26]([O:16][C:13]1[CH:14]=[C:15]2[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)=[CH:8][N:9]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:10]2=[N:11][CH:12]=1)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 59128696HCID 59128696, compound

Product 1

HCID 68609508HCID 68609508, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

According to the general procedure using: 27 (60 mg, 0.174 mmol), 1-bromobutane (143 mg, 1.05 mmol), K2CO3 (241 mg, 1.74 mmol) and n-Bu4NI (6.4 mg, 17 μmol) in acetone (4.0 mL) were heated at reflux for 22.5 h. Purification by PTLC using AcOEt:hexane=6:4 (v/v) as eluent gave 28j as a clear oil (48.7 mg, 70%).

Workup

  1. temperatureat reflux for 22.5 h
  2. customPurification by PTLC

Sources & evidence

ORD record
ord-d3cce9b432fd406295316ca4db410a34
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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