Potassium Carbonate → HCID 67114788, compound

HRID 881039Notes

Reaction equation

HRID 881039 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:11][CH2:10]3)[N:6]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14]C=3F)[N:5]=2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].ClC1C=CC([N+]([O-])=O)=C[N:30]=1>CS(C)=O>[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:10][CH2:11]3)[N:6]([C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:30]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 67114771HCID 67114771, compound

Product 1

HCID 67114788HCID 67114788, compoundYield 20.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of intermediate 3 (8.0 g, 54.05 mmol) and K2CO3 (27.96 g, 202.6 mmol) in DMSO (60 mL) was heated at 110° C. under nitrogen for 0.5 h. To the mixture, 2-chloro-5-nitro pyridine (12.8 g, 80.75 mmol) was added and stirred at the same temperature for 2 h. Work-up (H2O/AcOEt) and purification afforded the title compound (3.03 g). 1H-NMR (δ ppm, CDCl3, 400 MHz): 9.24 (d, J 2.6, 1H), 8.51 (dd, J 2.6, 9.9, 1H), 8.10 (d, J 9.2, 1H), 5.72 (s, 1H), 2.90-2.75 (m, 1H), 1.99-1.90 (m, 1H), 1.06-0.93 (m, 4H), 0.82-0.64 (m, 4H).

Workup

  1. custom(H2O/AcOEt) and purification

Sources & evidence

ORD record
ord-6fb25da0dedd41a79eef1a31626a8f56
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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