Sodium Hydroxide → 7-Iodo-3,4,5',6'-tetrahydro-2H,4'H-spiro[1-benzofuro[2,3-c]pyridine-1,3'-pyran]

HRID 1616927Notes

Reaction equation

HRID 1616927 reaction equation
[I:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([CH2:9][CH2:10][NH2:11])=[CH:7][O:8][C:4]=2[CH:3]=1.[O:14]1[CH2:19][CH2:18][CH2:17][C:16](=O)[CH2:15]1.[OH-].[Na+]>FC(F)(F)C(O)=O>[I:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]3[CH2:9][CH2:10][NH:11][C:16]4([CH2:17][CH2:18][CH2:19][O:14][CH2:15]4)[C:7]=3[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 901092H-Pyran-3(4H)-one, dihydro-HCID 67324004HCID 67324004, compound

Product 1

HCID 673239207-Iodo-3,4,5',6'-tetrahydro-2H,4'H-spiro[1-benzofuro[2,3-c]pyridine-1,3'-pyran]

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(6-iodo-benzofuran-3-yl)-ethylamine (1.00 g, 3.48 mmol) and dihydro-pyran-3-one (1.05 g, 10.4 mmol) in trifluoroacetic acid (4.00 mL) was heated at 80° C. for 15 h. The reaction mixture was cooled down, 1M aqueous NaOH was added and the mixture was extracted with DCM. The solvent was evaporated and the residue was purified by silica gel chromatography eluting with DCM-MeOH—NH4OH to afford the title product. mp 131-137° C. dec.; MS m/z 370 [M+H]+

Workup

  1. temperatureThe reaction mixture was cooled down
  2. extractionthe mixture was extracted with DCM
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with DCM-MeOH—NH4OH

Sources & evidence

ORD record
ord-794329f2a3f24b78bac8a95f2870735f
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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