Triphenylphosphine → 1-(2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)-3-phenylpropan-1-one

HRID 1408001Notes

Reaction equation

HRID 1408001 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1B1OC(C)(C)C(C)(C)O1)([O-:3])=[O:2].Br[C:26]1[CH:31]=[C:30]([C:32](=[O:41])[CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:29]=[CH:28][N:27]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C([O-])([O-])=O.[Na+].[Na+].C(COC)OC.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[CH:6][C:5]=1[C:28]1[CH:29]=[C:30]([C:32](=[O:41])[CH2:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:31]=[CH:26][N:27]=1)([O-:3])=[O:2]

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 66587487HCID 66587487, compoundHCID 867059361-(2-Bromopyridin-4-yl)-3-phenylpropan-1-one

Product 1

HCID 675181571-(2-(2-Nitro-5-(piperidin-1-yl)phenyl)pyridin-4-yl)-3-phenylpropan-1-oneYield 81.5%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 200 mg of 1-(4-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine 1.1e, 168 mg of 1-(2-bromopyridin-4-yl)-3-phenylpropan-1-one 5.1a, 12 mg of Pd(OAc)2, 58 mg of PPh3 in 1.25 mL of 2 N aqueous Na2CO3 solution and 3 mL of dimethoxyethane was refluxed for 4 h. The mixture was diluted with ethyl acetate and washed with water twice. The combined organic layer was dried over Na2SO4 and the solvent was evaporated. The residue was chromatographed on silica gel eluting with a gradient of 0% to 7% ethyl acetate in dichloromethane to give 196 mg of product.

Workup

  1. washwashed with water twice
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was chromatographed on silica gel eluting with a gradient of 0% to 7% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-bd6a3b6191084252bbde660ea77d52c7
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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