Potassium Carbonate → HCID 68451991, compound

HRID 2355067Notes

Reaction equation

HRID 2355067 reaction equation
Cl.[Br:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH:6]1[CH2:10][NH:9][CH2:8][CH2:7]1.Br[C:16]1[S:20][C:19]([C:21]#[N:22])=[N:18][N:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][C@H:6]1[CH2:7][CH2:8][N:9]([C:16]2[S:20][C:19]([C:21]#[N:22])=[N:18][N:17]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 533885265-Bromo-1,3,4-thiadiazole-2-carbonitrileHCID 53409201HCID 53409201, compound

Product 1

HCID 68451991HCID 68451991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 4-(2-bromophenoxy)pyrrolidine hydrochloride (0.5 g, 1.87 mmol) and 5-bromo-1,3,4-thiadiazole-2-carbonitrile (0.36 g, 1.87 mmol) in DMF (10 mL) was added K2CO3 (0.77 g, 5.61 mmol) under a nitrogen atmosphere. The mixture was stirred at 70° C. for 4 h. After dilution with water, the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and purified by preparative TLC with petroleum:EtOAc (2:1) to give the title compound. 1H NMR (300 MHz, CDCl3): δ 7.58 (d, 1H), 7.52 (t, 1H), 7.08 (t, 1H), 6.99 (d, 1H), 5.24 (m, 1H), 3.69-3.93 (m, 4H), 2.33-2.56 (m, 2H).

Workup

  1. extractionAfter dilution with water, the mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. custompurified by preparative TLC with petroleum:EtOAc (2:1)

Sources & evidence

ORD record
ord-672b6f16f4414f8c9913d70350e21785
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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