Dichloromethane → HCID 67813788, compound

HRID 2401390Notes

Reaction equation

HRID 2401390 reaction equation
[CH:1](/[N:14]=[CH:15]/[C:16]1[O:20][N:19]=[C:18]([CH3:21])[C:17]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)=[O:29])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.[Si]([C:44]#[N:45])(C)(C)C>C([O-])(O)=O.[Na+]>[CH:1]([NH:14][CH:15]([C:16]1[O:20][N:19]=[C:18]([CH3:21])[C:17]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28](=[O:29])[C:30]1[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[C:44]#[N:45])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 82115Trimethylsilyl cyanideHCID 178434776HCID 178434776, compound

Product 1

HCID 67813788HCID 67813788, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a round bottomed flask was added (E)-(2-(5-((benzhydrylimino)methyl)-3-methylisoxazol-4-yl)phenyl)(4-chlorophenyl)methanone (320 mg, 0.652 mmol), DCM (4.5 mL), and Yt(OTf)3 (40.4 mg, 0.065 mmol). To this solution was added TMS-CN (175 μl, 1.304 mmol) and the reaction was stirred overnight at room temperature. This solution was diluted with saturated aqueous NaHCO3. The layers were separated and the aqueous phase was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford the titled compound (300 mg, 0.579 mmol). LC/MS m/z 518 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-065db9b98b154a01b7cd06e9f44761f0
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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