Water → HCID 131725070, compound

HRID 585519Notes

Reaction equation

HRID 585519 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](Cl)=[O:8])=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][N:14]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][SiH3:29])[CH:23]=1)[C:15]2=[O:20].O.ClCCl>CN(C)C1C=CN=CC=1.O1CCCC1.N1C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:10][C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][N:14]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][SiH3:29])[CH:23]=2)[C:15]3=[O:20])=[O:8])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 178507381HCID 178507381, compound

Product 1

HCID 131725070HCID 131725070, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under argon and at 0° C., 5-chloro-2-thiophenecarbonyl chloride (1.7 g, 9.2 mmol) and 4-dimethylaminopyridine (93 mg, 0.8 mmol) are added to a solution of 4-amino-2-[3-(silylmethyl)benzyl]-1-isoindolinone (2.9 g, 7.7 mmol) in tetrahydrofuran (26 ml) and pyridine (12 ml). The reaction mixture is stirred at room temperature for 12 h, and water is added. After addition of dichloromethane and phase separation, the aqueous phase is extracted with dichloromethane. The combined organic phases are dried (sodium sulfate), filtered and concentrated under reduced pressure. The desired product is purified by flash chromatography (dichloromethane/methanol mixtures). Yield: 3.9 g, 97% of theory.

Workup

  1. extractionthe aqueous phase is extracted with dichloromethane
  2. dry with materialThe combined organic phases are dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe desired product is purified by flash chromatography (dichloromethane/methanol mixtures)

Sources & evidence

ORD record
ord-29c38e88d6cd4b3a872f7fa339f8d557
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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