Potassium Carbonate → HCID 56633567, compound

HRID 1355372Notes

Reaction equation

HRID 1355372 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[CH2:17]([N:24]1[CH2:29][C@@H:28]2[C@@H:26]([CH:27]2[NH2:30])[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:17]([N:24]1[CH2:29][C@@H:28]2[C@@H:26]([CH:27]2[NH:30][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 11084615HCID 11084615, compound

Product 1

HCID 56633567HCID 56633567, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Potassium carbonate (4.59 g, 33.2 mmol), followed by 1-fluoro-2-nitrobenzene (1.87 g, 13.3 mmol) were added to a solution of (1R,5S)-3-benzyl-3-azabicyclo[3.1.0]hex-6-ylamine (WO 9318001), (2.50 g, 13.3 mmol) in N,N-dimethylformamide (40 ml), and the reaction mixture stirred at 130° C. for 18 hours. The cooled mixture was filtered, and the filtrate concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, the phases separated, and the aqueous layer extracted with ethyl acetate (3×). The combined organic solutions were washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure. The residual brown oil was purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (95:5 to 90:10) to afford the title compound as an orange crystalline foam, 3.11 g.

Workup

  1. filtrationThe cooled mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe phases separated
  5. extractionthe aqueous layer extracted with ethyl acetate (3×)
  6. washThe combined organic solutions were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residual brown oil was purified by column chromatography on silica gel using an elution gradient of pentane:ethyl acetate (95:5 to 90:10)

Sources & evidence

ORD record
ord-88e3107e06a34e74a454a423066028c1
Source dataset
uspto-grants-2003_07
Patent number
US06586430B1

Reaction notes

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