Water → HCID 87324728, compound

HRID 1035315Notes

Reaction equation

HRID 1035315 reaction equation
[CH2:1]1[N:11]2[C@@H:5]([CH2:6][CH2:7][O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=32)[CH2:4][NH:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][F:25].O>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[F:25][CH2:24][CH2:23][N:3]1[CH2:2][CH2:1][N:11]2[C@@H:5]([CH2:6][CH2:7][O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=32)[CH2:4]1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 66770002HCID 66770002, compound

Product 1

HCID 87324728HCID 87324728, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of Example 169 (430 mg 2.1 mmol) in N,N-dimethylformamide (10 mL) was added K2CO3 (582 mg, 4.21 mmol) followed by 1-bromo-2-fluoroethane (267 mg, 2.1 mmol). The reaction stirred at room temperature for 16 hours before addition of water, brine and ethyl acetate. The organic layer was collected and concentrated. Purification via flash chromatography (0-100% ethyl acetate/hexanes) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 6.69-7.00 (m, 4H), 4.64 (t, J=4.96 Hz, 1H), 4.48 (t, J=4.76 Hz, 1H), 4.28-4.43 (m, 1H), 4.03-4.15 (m, 1H), 2.97-3.21 (m, 3H), 2.57-2.86 (m, 4H), 2.33-2.46 (m, 1H), 2.19-2.33 (m, 1H), 1.80-2.08 (m, 2H); MS (ESI+) m/z 251 (M+H)+.

Workup

  1. customThe organic layer was collected
  2. concentrationconcentrated
  3. customPurification via flash chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6e4525e0cfab4c7182416eec082acede
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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