Potassium Carbonate → HCID 44481359, compound

HRID 452398Notes

Reaction equation

HRID 452398 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[C:10]([S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[CH:11]=[CH:12][C:6]=2[CH2:5][O:4]1.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:17][C:16]([F:19])([F:18])[S:13]([C:10]1[CH:11]=[CH:12][C:6]2[CH2:5][O:4][CH:3]([CH2:2][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:8][C:7]=2[CH:9]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 67155666HCID 67155666, compound

Product 1

HCID 44481359HCID 44481359, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(bromomethyl)-7-[(trifluoromethyl)sulfonyl]-4H-1,3-benzodioxine (0.40 g, 1.11 mmol), pyrrolidine (0.47 ml, 5.5 mmol), potassiumcarbonate (0.23 g, 1.7 mmol) and ACN (3.0 ml) was heated in a micro wave oven at 150° C. for 15 min. The mixture was filtered and evaporated to dryness. The residue was purified two times on a silica column using EtOAc/MeOH (4:1) and EtOAc/MeOH (9:1) as eluents. The pure fractions were collected and evaporated to afford the title product (0.19 g, 48%). The amine was converted into the fumaric acid salt and crystallized from EtOH/MeOH/DEE. M.p. 184° C. MS m/z (rel. intensity, 70 eV) 351 (M+, 5), 85 (6), 84 (bp), 76 (5), 55 (4).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness
  3. customThe residue was purified two times on a silica column
  4. customThe pure fractions were collected
  5. customevaporated

Sources & evidence

ORD record
ord-3a9fb56fce394da6be498db4b7b1336b
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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