Potassium Carbonate → HCID 58266689, compound

HRID 1505902Notes

Reaction equation

HRID 1505902 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][C@H:18]1[O:23][C@@H:22]([CH3:24])[CH2:21][NH:20][CH2:19]1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:20]2[CH2:19][C@H:18]([CH3:17])[O:23][C@H:22]([CH3:24])[CH2:21]2)=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6415002,6-Dimethylmorpholine, cis-HCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 58266689HCID 58266689, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 4-bromo-2-fluorobenzyl bromide (1.0 g, 3.7 mmol) and potassium carbonate (0.61 g, 4.4 mmol) in THF (37 mL) was added cis-2,6-dimethylmorpholine (0.43 g, 3.7 mmol). The reaction mixture was heated under reflux for 6 h and then cooled, the solid removed by filtration and the filtrate was evaporated. The resultant residue was loaded onto a 10 g SCX-2 cartridge which was washed with methanol then 2N ammonia in methanol. Concentration of the combined basic fractions in vacuo afforded the title compound (76 mg, 7%). 1H NMR (CDCl3, 300 MHz): 7.28-7.19 (m, 3H), 3.73-3.59 (m, 2H), 3.49 (d, J=1.5 Hz, 2H), 2.71-2.64 (m, 2H), 1.86-1.73 (m, 2H), 1.14 (d, J=6.3 Hz, 6H). LCMS (Method G): RT=2.84 min, M+H+=302.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 6 h
  3. temperaturecooled
  4. customthe solid removed by filtration
  5. customthe filtrate was evaporated
  6. washwas washed with methanol

Sources & evidence

ORD record
ord-b5d2c665dee84113a7b6d3fc1eb5e640
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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