Water → HCID 65341357, compound

HRID 1051530Notes

Reaction equation

HRID 1051530 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:18][CH:15]2[CH2:16][CH2:17][O:12][CH2:13][CH2:14]2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4192234-AminotetrahydropyranHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 65341357HCID 65341357, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (1.1 g, 4.95 mmol) and tetrahydro-2H-pyran-4-amine (500 mg, 4.95 mmol) in DMF (6 mL) was added K2CO3 (1.37 g, 9.9 mmol) and the mixture stirred in sealed tube at 85° C. for 16 h. After cooling, water (100 mL) was added to the mixture and extracted with DCM (3×50 mL). The combined organic layers were washed with water (2×50 mL), brine (50 mL) and dried over anhydrous Na2SO4 then filtered and concentrated to yield the title compound which was directly used for next step without further purification.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with DCM (3×50 mL)
  3. washThe combined organic layers were washed with water (2×50 mL), brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationthen filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7dc8e77959e14ff5be63d49ec3ef46e4
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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