Potassium Carbonate → HCID 22281800, compound

HRID 1062599Notes

Reaction equation

HRID 1062599 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[CH2:4][N:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]2[C:13]([CH3:23])=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[N:15]=[C:6]12.Br[CH2:30][CH:31]1[CH2:33][CH2:32]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[C:3]=1[CH2:4][N:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]2[C:13]([CH3:23])=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:30][CH:31]4[CH2:33][CH2:32]4)=[CH:20][CH:21]=3)[N:15]=[C:6]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane2×HCID 9955190HCID 9955190, compound

Product 1

HCID 22281800HCID 22281800, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the compound obtained in Example 23 (0.25 g, 0.56 mmol) in DMF (30 ml) is added (bromomethyl)cyclopropane (0.114 g, 0.84 mmol), K2CO3 (0.116 g, 0.84 mmol) and KI (0.047 g, 0.28 nmol). The residual reaction mixture is stirred at 60° C. for 4 hours. To this mixture is added (bromomethyl)cyclopropane (0.14 g, 1.0 mmol). It is stirred at this temperature for 21 hours and is evaporated under reduced pressure to afford the residue, which is partitioned between chloroform (100 ml) and aqueous saturated NaHCO3 solution (30 ml). The aqueous layer is extracted with chloroform (30 ml). The combined organic extract is dried over Na2SO4 and concentrated under reduced pressure to give the residue, which is chromatographed on silica gel to afford white crystals (0.23 g, 82%).

Workup

  1. customThe residual reaction mixture
  2. stirringIt is stirred at this temperature for 21 hours
  3. customis evaporated under reduced pressure
  4. customto afford the residue, which
  5. customis partitioned between chloroform (100 ml) and aqueous saturated NaHCO3 solution (30 ml)
  6. extractionThe aqueous layer is extracted with chloroform (30 ml)
  7. extractionThe combined organic extract
  8. dry with materialis dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto give the residue, which
  11. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-0a892c55de9743f881eb76859f00b785
Source dataset
uspto-grants-2005_11
Patent number
US06962919B2

Reaction notes

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