Sodium Carbonate → 2-(2-Nitro-5-(piperidin-1-yl)phenyl)isonicotinaldehyde

HRID 1408003Notes

Reaction equation

HRID 1408003 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].Cl[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][N:33]=1)[CH:29]=[O:30].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC>[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:26]1[CH:27]=[C:28]([CH:31]=[CH:32][N:33]=1)[CH:29]=[O:30])([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27629942-Chloro-4-pyridinecarboxaldehydeHCID 66587487HCID 66587487, compound

Product 1

HCID 867059382-(2-Nitro-5-(piperidin-1-yl)phenyl)isonicotinaldehyde

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 200 mg of 1-(4-nitro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine 1e, 85 mg of 2-chloroisonicotinaldehyde, 6.7 mg of Pd(OAc)2, 31 mg of PPh3, 1.25 mL of 2 N aqueous Na2CO3 solution, and 3 mL of DME were refluxed 2 h. The mixture was diluted with ethyl acetate and washed 3× with water. The organic extracts were washed with brine and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel eluting with 10% ethyl acetate in dichloromethane. This gave 114 mg of product. MS (ES, m/z): 312.0 [M+H]+.

Workup

  1. temperaturewere refluxed 2 h
  2. washwashed 3× with water
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed on silica gel eluting with 10% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-0ad3158d179d4eea842a88fa5574ca90
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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