Bis(pyridine)iodonium tetrafluoroborate → 3-Iodo-6-methoxy-7-(4-methoxy-benzyloxy)-2-(1-methyl-1H-pyrazol-4-yl)-furo[3,2-b]pyridine

HRID 1258435Notes

Reaction equation

HRID 1258435 reaction equation
C[O:2][C:3]1[C:4]([C:21]#[C:22][C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)=[N:5][CH:6]=[C:7]([O:19][CH3:20])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.F[B-](F)(F)F.[IH2+:34].N1C=CC=CC=1.N1C=CC=CC=1>C1COCC1>[I:34][C:21]1[C:4]2=[N:5][CH:6]=[C:7]([O:19][CH3:20])[C:8]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:3]2[O:2][C:22]=1[C:23]1[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=1

Participants

4

Reactant 2

HCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 686980513,5-dimethoxy-4-(4-methoxy-benzyloxy)-2-(1-methyl-1H-pyrazol-4-ylethynyl)pyridine

Product 1

HCID 686957033-Iodo-6-methoxy-7-(4-methoxy-benzyloxy)-2-(1-methyl-1H-pyrazol-4-yl)-furo[3,2-b]pyridineYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3,5-dimethoxy-4-(4-methoxy-benzyloxy)-2-(1-methyl-1H-pyrazol-4-ylethynyl)pyridine (80 mg, 0.21 mmol) in dry THF (2 ml) was added bispyridine iodonium tetrafluoroborate (94 mg, 0.25 mmol) and the reaction was refluxed for 0.5 hours. After cooling, the reaction was quenched with 10% Na2S2O3 (aq) and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated onto silica-gel under reduced pressure. The solid residue was purified by flash chromatography (silica-gel, eluted with EtOAc:hexanes, 3:2) to give the product as a white solid (65 mg, 63%). 1H—NMR (300 MHz, CDCl3) δ 8.23 (s, 1H), 8.16 (s, 1H), 8.15 (s, 1H), 7.38 (d, J=8.6 Hz, 2H), 6.86 (d, J=8.6 Hz, 2H), 5.60 (s, 2H), 3.99 (s, 3H), 3.93 (s, 3H), 3.77 (s, 3H).

Workup

  1. temperaturethe reaction was refluxed for 0.5 hours
  2. temperatureAfter cooling
  3. customthe reaction was quenched with 10% Na2S2O3 (aq)
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated onto silica-gel under reduced pressure
  8. customThe solid residue was purified by flash chromatography (silica-gel, eluted with EtOAc:hexanes, 3:2)

Sources & evidence

ORD record
ord-ce1bd6a0577345fbb1cab9257ccf837f
Source dataset
uspto-grants-2013_06
Patent number
US08466163B2

Reaction notes

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