1-Bromo-2-Chloroethane → HCID 67985006, compound

HRID 705378Notes

Reaction equation

HRID 705378 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:10]([C:11]3[NH:15][C:14](=[O:16])[O:13][N:12]=3)=[C:4]2[CH:3]=1.Br[CH2:26][CH2:27][Cl:28].N12CCCN=C1CCCCC2>CN(C)C(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:10]([C:11]3[N:15]([CH2:26][CH2:27][Cl:28])[C:14](=[O:16])[O:13][N:12]=3)=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136621555HCID 136621555, compound

Product 1

HCID 67985006HCID 67985006, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of Example 19H (0.64 g, 1.653 mmol), 1-bromo-2-chloroethane (0.206 mL, 2.479 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.374 mL, 2.479 mmol) in N,N-dimethylacetamide (8 mL) was heated at 100° C. for 20 hours, cooled and partitioned with ethyl acetate and 1 M aqueous HCl. The organic layer was washed with brine twice, dried with sodium sulfate, filtered and concentrated. Purification on a 40 g silica cartridge eluting with 1-2% methanol in dichloromethane provided the title compound as a solid (0.139 g, 19%). MS (ESI+) m/z 449/451 (M+H)+.

Workup

  1. temperaturecooled
  2. custompartitioned with ethyl acetate and 1 M aqueous HCl
  3. washThe organic layer was washed with brine twice
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on a 40 g silica cartridge
  8. washeluting with 1-2% methanol in dichloromethane

Sources & evidence

ORD record
ord-fb70accf0c0c4ac9ae9ff8e12201f5ba
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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