2-Fluoroethyl bromide → HCID 18705798, compound

HRID 2287844Notes

Reaction equation

HRID 2287844 reaction equation
[H-].[Na+].[CH2:3]([N:6]([CH2:22][CH2:23][CH3:24])[CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:19][CH2:20][CH3:21])=[C:12]([C:16]([NH2:18])=[O:17])[CH:13]=2)[CH2:8]1)[CH2:4][CH3:5].Br[CH2:26][CH2:27][F:28]>CCCCCC.CN(C=O)C>[CH2:22]([N:6]([CH2:3][CH2:4][CH3:5])[CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([O:19][CH2:20][CH3:21])=[C:12]([C:16]([NH:18][CH2:26][CH2:27][F:28])=[O:17])[CH:13]=2)[CH2:8]1)[CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 9817956HCID 9817956, compound

Product 1

HCID 18705798HCID 18705798, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Procedure

Sodium hydride (0.05 g, 1.2 mmol) was washed with hexane under nitrogen and suspended in DMF (5 mL). 2-(Dipropylamino)-6-ethoxy-2,3-dihydro-1H-indene-5-carboxamide (81, 0.15 g, 0.5 mmol) in DMF (5 mL) was added dropwise at 0-5° C. over 30 min and the mixture stirred 30 min. 1-Bromo-2-fluoroethane (0.26 g, 2 mmol) in DMF (5 mL) was added and the resulting mixture was stirred 3 h. The reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer is washed with water, brine, dried (MgSO4), filtered and concentrated to give crude product. Chromatographic purification yielded pure product 85 as an oil that was converted into the HCl salt and crystallized from EtOAc/hexane/MeOH to give a white solid (m.p. 158-159° C.).

Workup

  1. stirringthe resulting mixture was stirred 3 h
  2. customThe reaction was quenched with saturated NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layer is washed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude product
  9. customChromatographic purification

Sources & evidence

ORD record
ord-2e7302551c3d48fcb1b728f651936238
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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