Hydrochloric Acid → HCID 86719346, compound

HRID 922378Notes

Reaction equation

HRID 922378 reaction equation
Br[C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[CH3:10][S:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C=O)C>[CH3:10][S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:2]2[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15]1)(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 7091611-(Methylsulfonyl)piperazineHCID 27570096-Bromopyridine-2-carbaldehyde

Product 1

HCID 86719346HCID 86719346, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 6-bromopicolinaldehyde (1.50 g, 8.10 mmol), 1-(methylsulfonyl)piperazine (9, 5.30 g, 32.2 mmol), potassium carbonate (4.45 g, 32.2 mmol) and anhydrous DMF (10 mL) was placed in a sealed vessel and the mixture was heated at 120° C. for 20 h. The mixture was diluted with water (50 mL) and brought to pH 7 using 2 N aq. HCl (15 mL). The resulting solution was extracted with CH2Cl2 (3×50 mL) and the combined extracts were washed with brine (200 mL). The solution was dried (MgSO4), filtered, concentrated, and purified by silica gel chromatography eluting with 0-3% CH3OH in CH2Cl2 to afford the title compound (0.441 g, 20%) as an orange oil: 1H NMR (500 MHz, CDCl3) δ 9.90 (s, 1H), 7.67 (t, J=8.0 Hz, 1H), 7.34 (d, J=7.0 Hz, 1H), 6.89 (d, J=8.5 Hz, 1H), 3.80-3.78 (m, 4H), 3.37-3.33 (m, 4H), 2.81 (s, 3H).

Workup

  1. customwas placed in a sealed vessel
  2. extractionThe resulting solution was extracted with CH2Cl2 (3×50 mL)
  3. washthe combined extracts were washed with brine (200 mL)
  4. dry with materialThe solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography
  8. washeluting with 0-3% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-7254a98b09cf4ec09bbfb039e1d8b9e8
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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