Potassium Carbonate → 4-[4-[4-(Trifluoromethoxy)phenyl]-2-pyridinyl]benzaldehyde

HRID 1192802Notes

Reaction equation

HRID 1192802 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.ClC1C=C(I)C=CN=1.[CH:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[F:16][C:15]([F:18])([F:17])[O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:32]3[CH:33]=[CH:34][C:29]([CH:27]=[O:28])=[CH:30][CH:31]=3)[CH:7]=2)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 15165112-Chloro-4-iodopyridineHCID 115871572-Chloro-4-[4-(trifluoromethoxy)phenyl]pyridine

Product 1

HCID 578244174-[4-[4-(Trifluoromethoxy)phenyl]-2-pyridinyl]benzaldehydeYield 63.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-4-(4-trifluoromethoxyphenyl)-pyridine (0.55 mmol) starting from 2-chloro-4-iodopyridine, 4-formylphenyl boronic acid (0.82 mmol), tetrakis(triphenylphosphine)palladium(0) (0.005 mmol), 2 M potassium carbonate (0.55 mL) and dioxane (3 mL) were combined in a vial and irradiated by microwave for 15 min at 150° C. The reaction mixture was taken up in EtOAc and washed with brine. The organic layer was dried over magnesium sulfate, was filtered and the solvent removed in vacuo. Purification by silica gel chromatography (EtOAc/hexanes) yielded the product (120 mg) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 10.11 (s, 1H), 8.81 (d, J=4.8 Hz, 1H), 8.24 (d, J=8.7 Hz, 2H), 8.03 (d, J=8.4 Hz, 2H), 7.96 (m, 1H), 7.73 (d, J=9.0 Hz, 2H), 7.49 (dd, J=5.3, 1.8 Hz, 1H), 7.37 (d, J=8.1 Hz, 2H); EIMS m/z 343 (M+).

Workup

  1. customirradiated by microwave for 15 min at 150° C
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationwas filtered
  5. customthe solvent removed in vacuo
  6. customPurification by silica gel chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-208954b53d4648c39747f7e2b3d126fd
Source dataset
uspto-grants-2014_03
Patent number
US08680269B2

Reaction notes

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