2-Bromopyridine → HCID 18398987, compound

HRID 1019395Notes

Reaction equation

HRID 1019395 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[C:22]3[C:17](=[CH:18][C:19]([OH:43])=[C:20]([O:41][CH3:42])[CH:21]=3)[C:16]2=[O:44])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu](I)I>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]([C:29]3[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=3)[C:22]3[C:17](=[CH:18][C:19]([O:43][C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=4)=[C:20]([O:41][CH3:42])[CH:21]=3)[C:16]2=[O:44])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 18399114HCID 18399114, compound

Product 1

HCID 18398987HCID 18398987, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of the compound obtained in Example 5 (300 mg), 2-bromopyridine (57 μl), copper iodide (113 mg) and potassium carbonate (82 mg) in dimethylformamide (5 μl) is heated with stirring at 80° C. for five hours. After the reaction is complete, the reaction mixture is extracted with ethyl acetate. The extract is washed with aqueous ammonia, and further washed with water, dried, and concentrated under reduced pressure. The residue is purified by Chromatotron (solvent; hexane:ethyl acetate=1:1) to give 2-[4-(tert-butoxycarbonylamino)phenyl]-6-methoxy-3-methoxycarbonyl-7-(2-pyridyloxy)-4-(3,4,5-trimethoxyphenyl)-1(2H)-isoquinolinone (40 rag) as listed in Table 20.

Workup

  1. temperatureis heated
  2. extractionthe reaction mixture is extracted with ethyl acetate
  3. washThe extract is washed with aqueous ammonia
  4. washfurther washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by Chromatotron (solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-bad48635fa3244e8809dddd1177ece23
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

Loading…