Water → 2-{4-[3-(3,5-Difluorophenyl)prop-2-yn-1-ylidene]piperidin-1-yl}-6-methoxy-3-nitropyridine

HRID 1895984Notes

Reaction equation

HRID 1895984 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH:11]=[C:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21]([O:28][CH3:29])[N:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH:11]=[C:12]2[CH2:13][CH2:14][N:15]([C:19]3[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21]([O:28][CH3:29])[N:20]=3)[CH2:16][CH2:17]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27950292-Chloro-6-methoxy-3-nitropyridineHCID 866273424-[3-(3,5-Difluorophenyl)prop-2-ynylidene]piperidine

Product 1

HCID 251819212-{4-[3-(3,5-Difluorophenyl)prop-2-yn-1-ylidene]piperidin-1-yl}-6-methoxy-3-nitropyridineYield 83.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of Compound 228b (0.046 mg, 0.197 mmol), 2-chloro-6-methoxy-3-nitropyridine (34.6 mg, 0.18 mmol), potassium carbonate (50.3 mg, 0.36 mmol) in N,N-dimethylacetamide was heated in a microwave oven at 165° C. for 3 min. Afterwards, the reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether 5:95) affording the title product (0.058 g).

Workup

  1. temperatureAfterwards, the reaction mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto afford a residue, which
  7. customwas purified by flash chromatography (EtOAc—Petroleum Ether 5:95)

Sources & evidence

ORD record
ord-fdec287c04e847e8adedd4585571844d
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

Loading…