1,2-Dibromoethane → HCID 11477177, compound

HRID 130662Notes

Reaction equation

HRID 130662 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[C:26]5[C:21](=[CH:22][C:23]([OH:27])=[CH:24][CH:25]=5)[N:20]=[CH:19][CH:18]=4)=[CH:15][C:10]=3[O:9][C:8]=2[CH3:28])=[O:6])[CH2:3][CH2:2]1.[Br:29][CH2:30][CH2:31]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:29][CH2:30][CH2:31][O:27][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([O:16][C:14]3[CH:13]=[CH:12][C:11]4[C:7]([C:5]([NH:4][CH:1]5[CH2:2][CH2:3]5)=[O:6])=[C:8]([CH3:28])[O:9][C:10]=4[CH:15]=3)=[CH:18][CH:19]=[N:20]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 136090311HCID 136090311, compound

Product 1

HCID 11477177HCID 11477177, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 90-G (1.4 g, 3.7 mmol), Br(CH2)2Br 90-H (2.1 g, 11.2 mmol) and K2CO3 (1.5 g, 11.2 mmol) in DMF (40 ml) was heated to 50° C. overnight. The reaction mixture was extracted with EtOAc. The concentrated residue was purified by silica gel column chromatography using 5% MeOH/CH2Cl2 to yield 6-{[7-(2-bromoethoxy)quinolin-4-yl]oxy}-N-cyclopropyl-2-methyl-1-benzofuran-3-carboxamide 90-1 (1.1 g, 61%).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. customThe concentrated residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c0357f8c84c24ffb8d0ff8d45a4d4451
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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