1,3-Dibromopropane → HCID 10200722, compound

HRID 1822833Notes

Reaction equation

HRID 1822833 reaction equation
[CH2:1]([C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:19]([NH2:21])=[O:20])[CH3:2].[C:26]([O-:29])([O-])=O.[Cs+].[Cs+].Br[CH2:33][CH2:34]CBr>CS(C)=O>[CH2:1]([C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:33][CH2:34][CH2:26][OH:29])=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]=[CH:8][C:7]=1[C:19]([NH2:21])=[O:20])[CH3:2]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 135788285HCID 135788285, compound

Product 1

HCID 10200722HCID 10200722, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(2-ethylanilino)-7-hydroxy-6-methoxy-3-quinolinecarboxamide (0.12 g, 0.35 mmol), DMSO (15 ml), Cs2CO3 (0.34 g, 1.0 mmol), and 1,3-dibromopropane was stirred at 100° C. for 2 h. The reaction mixture was poured out on NaHCO3 (aq) and extracted with CH2Cl2. The substance was chromatographed on furnishing the title compound (0.012 g, 9%).

Workup

  1. additionThe reaction mixture was poured out on NaHCO3 (aq)
  2. extractionextracted with CH2Cl2
  3. customThe substance was chromatographed

Sources & evidence

ORD record
ord-6dee1f6ad89d40ab88ca7b4e57831763
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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