N-Iodosuccinimide → HCID 69478504, compound

HRID 1183203Notes

Reaction equation

HRID 1183203 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:17][C@@H:16]3[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=2)[N:6]=[CH:5]1.[I:23]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>ClCCl.FC(F)(F)C(O)=O>[F:1][CH2:2][CH2:3][N:4]1[C:8]([I:23])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:17][C@@H:16]3[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=2)[N:6]=[CH:5]1

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 86664898HCID 86664898, compound

Product 1

HCID 69478504HCID 69478504, compoundYield 17.3%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl (1S,2S)-2-{4-[1-(2-fluoroethyl)-1H-imidazol-4-yl]phenyl}cyclopropanecarboxylate (450 mg, 1.488 mmol) in dichloromethane (5 mL) was added N-iodosuccinimide (352 mg, 1.563 mmol) and three drops trifluoroacetic acid. The reaction was stirred at rt for 3 h. The mixture was neutralized with aqueous sodium bicarbonate and the organics were extracted with dichloromethane. The organics were then washed with aqueous sodium thiosulfate, followed by three washes with water. The organics were dried (MgSO4), concentrated, and purified on 20 g of silica gel eluting a gradient of 35-100% ethyl acetate in hexanes to give rise to the title compound as a brown oil (110 mg, 0.257 mmol). LCMS: [M+1]+=429.

Workup

  1. extractionthe organics were extracted with dichloromethane
  2. washThe organics were then washed with aqueous sodium thiosulfate
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified on 20 g of silica gel eluting a gradient of 35-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d38cf30e76554b9f8ac7bce9d14cdf6d
Source dataset
uspto-grants-2014_03
Patent number
US08664253B2

Reaction notes

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