1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 58961600, compound

HRID 916934Notes

Reaction equation

HRID 916934 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:14][C:13](=[O:15])[C:12]([C:16]#[N:17])=[CH:11][C:10]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.Br[CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:10]2[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[N:14][C:13]([O:15][CH2:26][CH2:27][N:28]3[C:29](=[O:38])[C:30]4[C:31](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]3=[O:33])=[C:12]([CH:11]=2)[C:16]#[N:17])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 219848256-(2,4-Dichlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 58961600HCID 58961600, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To the product of Step B Example 19 (600 mg, 1.597 mmol) was added N-(2-bromoethyl)-phthalimide (690 mg, 2.715 mmol), K2CO3 (331 mg, 2.396 mmol) and DMF (8 mL). The mixture was heated to 70° C. for 20 hours. The mixture was filtered, concentrated and passed through a short plug of silica gel eluting with 33% ethyl acetate/hexane. The partially purified material was carried on without further purification. MS (electrospray) m/e 547.8 MH+ (retention time=4.4 min LC/MS).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe partially purified material was carried on without further purification

Sources & evidence

ORD record
ord-42fb3a302b5b49a29257d121b5d51ab2
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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