Diiodomethane → HCID 117839793, compound

HRID 1477649Notes

Reaction equation

HRID 1477649 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH:9]=2)=[CH:4][CH:3]=1.[CH2:14]([Zn]CC)C.ICI.[Cl-].[NH4+]>C(Cl)(Cl)Cl.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[CH2:14][CH:9]2[CH:10]([NH2:13])[CH2:11][CH2:12]3)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 65174758HCID 65174758, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 117839793HCID 117839793, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (0.28 mL) of 3-(4-fluorophenyl)cyclopent-2-enamine (55.8 mg, 0.315 mmol) synthesized in Reference Synthesis Example 223, diethylzinc (15% solution in toluene) (162 μL, 1.78 mmol) was added and then diiodomethane (127 μL, 1.58 mmol) was added at 0° C. with stirring and the resultant mixture was stirred at room temperature for 1 day. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction from the resultant mixture with chloroform was performed. The organic layer was concentrated under reduced pressure to obtain a crude product of the title compound.

Workup

  1. additionwas added
  2. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-536c4610137443938e961fa619c614eb
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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