Water → 3-(6-Methylpyridin-2-yl)-1-[1-(3-nitropyridin-2-yl)piperidin-4-yl]prop-2-yn-1-ol

HRID 1895993Notes

Reaction equation

HRID 1895993 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][CH:10]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[OH:11])[CH:5]=[CH:4][CH:3]=1.Br[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=1.C(N(CC)CC)C.O>CN(C)C(=O)C>[CH3:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][CH:10]([CH:12]2[CH2:13][CH2:14][N:15]([C:19]3[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:16][CH2:17]2)[OH:11])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5550542-Bromo-3-nitropyridineHCID 689774953-(6-Methyl-pyridin-2-yl)-1-piperidin-4-yl-prop-2-yn-1-ol

Product 1

HCID 687246183-(6-Methylpyridin-2-yl)-1-[1-(3-nitropyridin-2-yl)piperidin-4-yl]prop-2-yn-1-olYield 74.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A well homogenised mixture of Compound 237a (200 mg, 0.86 mmol), 2-bromo-3-nitropyridine (194 mg, 0.95 mmol) and triethylamine (249 μL, 1.74 mmol) in N,N-dimethylacetamide (15 mL) was stirred at r.t. for 4 h. Afterwards, the reaction mixture was 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 eluting with Petroleum Ether-EtOAc 7:3, affording the title product (225 mg) as a yellow oil.

Workup

  1. stirringwas stirred at r.t. for 4 h
  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
  8. washeluting with Petroleum Ether-EtOAc 7:3

Sources & evidence

ORD record
ord-2142db12e38e4ba88e795be5a27ccf19
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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