Potassium Carbonate → HCID 66599976, compound

HRID 1812111Notes

Reaction equation

HRID 1812111 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.[NH:10]1[CH2:15][CH2:14][S:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][N:10]2[CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 220506385-(Bromomethyl)-2-fluoropyridine

Product 1

HCID 66599976HCID 66599976, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-(bromomethyl)-2-fluoropyridine (3.61 g, 19.00 mmol) in anhydrous DMF (22 mL) at 0° C. was treated with thiomorpholine (2.254 g, 21.85 mmol) (TCI America) in 3 mL of DMF and potassium carbonate (3.28 g, 23.75 mmol). The suspension was slowly warmed to RT and stirred at RT for 2 h. The reaction was quenched with 30 mL of ice water, stirred at RT for 30 min, and the solid was collected by filtration, and rinsed with water followed by ether to give 4-((6-fluoropyridin-3-yl)methyl)thiomorpholine (3.33 g, 15.69 mmol, 83% yield) as an off-white crystalline solid. 1H NMR (400 MHz, d6-DMSO) δ 8.12 (s, 1H); 7.89 (td, J=8.20, 2.2 Hz, 1H); 7.14 (dd, J=8.10, 2.80 Hz, 1H); 3.53 (s, 2H); 2.63-2.59 (br. 8H). m/z (ESI, +ve ion) 213 (M+H)+.

Workup

  1. customThe reaction was quenched with 30 mL of ice water
  2. stirringstirred at RT for 30 min
  3. filtrationthe solid was collected by filtration
  4. washrinsed with water

Sources & evidence

ORD record
ord-bb05c1d5de4042b49fb2716e42798aa8
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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