1-Bromo-3-chloropropane → HCID 10451974, compound

HRID 902039Notes

Reaction equation

HRID 902039 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=3)=[N:10][N:11]3[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:12]=23)=[CH:4][CH:3]=1.Br[CH2:27][CH2:28][CH2:29]Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.O>[CH2:29]([O:18][CH2:17][C:15]1[CH:14]=[CH:13][C:12]2[N:11]([N:10]=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=3)[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH:16]=1)[CH:28]=[CH2:27]

Participants

7

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 10359469HCID 10359469, compound

Product 1

HCID 10451974HCID 10451974, compoundYield 27.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of EXAMPLE 99 (0.13 g, 0.39 mmol) and 1-bromo-3-chloropropane (0.06 g, 0.39 mmol) in DMF (10 mL) was treated with cesium carbonate (0.14 g, 0.43 mmol) and heated to 80° C. The reaction is stirred overnight and is diluted with EtOAc and water. The organic phase is separated and washed with brine. After drying over Na2SO4, the organic phase is filtered, and the solvent removed to afford 0.04 g (27%) of product. MS ES+ m/e 374.0 (M+1).

Workup

  1. customThe organic phase is separated
  2. washwashed with brine
  3. dry with materialAfter drying over Na2SO4
  4. filtrationthe organic phase is filtered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-1f0254be948845bd9467dd9cb73ba95a
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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