Cesium carbonate → HCID 86690872, compound

HRID 1465570Notes

Reaction equation

HRID 1465570 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[S:12][CH:13]=2)=[C:4]([CH3:23])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:31]1[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[N:35][CH:36]=1>CN(C=O)C>[CH3:8][C:6]1[CH:7]=[C:2]([O:1][C:31]2[CH:36]=[N:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)[CH:3]=[C:4]([CH3:23])[C:5]=1[C:9]1[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[S:12][CH:13]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 8176205-Bromo-2-nitropyridineHCID 86690827HCID 86690827, compound

Product 1

HCID 86690872HCID 86690872, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 5-3 (1.92 g, 5.91 mmol) in DMF (15 mL) was added with cesium carbonate (2.41 g, 7.39 mmol). The reaction mixture was heated at 50° C. for 60 min and added with 5-bromo-2-nitropyridine (24-1, 1.80 g). The reaction mixture was heated at 50° C. for 4.0 h. The solution was quenched with water (40 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=3/1-1/3) to give 24 (1.76 g) in 67% yield: 1H NMR (500 MHz, DMSO-d6) δ 8.78 (d, 2 H), 8.42 (d, 1 H), 8.33 (d, 1 H), 7.96 (d, 2 H), 7.63 (m, 1 H), 7.21 (s, 1 H), 7.01 (s, 2 H), 2.08 (s, 6 H), ESI-MS=m/z 447.5 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 4.0 h
  2. customThe solution was quenched with water (40 mL)
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=3/1-1/3)

Sources & evidence

ORD record
ord-59f79e2287f24700840204c3be231266
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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