N-bromobutanimide → (trans) 9-(4-fluoro-3-iodophenyl)-3-methyl-5,9-dihydro-3H-furo[3,4-b]pyrano[4,3-e]pyridine-1,8(4H,7H)-dione

HRID 987390Notes

Reaction equation

HRID 987390 reaction equation
[CH2:1]([C:3]1[NH:8][C:7]2[CH2:9][O:10][CH2:11][C:12](=[O:13])[C:6]=2[CH:5]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([I:21])[CH:15]=2)[C:4]=1[C:22]([O:24]C)=[O:23])[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)Cl>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:5]2[C:6]3[C:12](=[O:13])[CH2:11][O:10][CH2:9][C:7]=3[NH:8][C:3]3[C@H:1]([CH3:2])[O:24][C:22](=[O:23])[C:4]2=3)=[CH:15][C:16]=1[I:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18008672methyl 2-ethyl-4-(4-fluoro-3-iodophenyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridin-3-carboxylate

Product 1

HCID 86587546(trans) 9-(4-fluoro-3-iodophenyl)-3-methyl-5,9-dihydro-3H-furo[3,4-b]pyrano[4,3-e]pyridine-1,8(4H,7H)-dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The product from Example 11B (2.8 g, 6.1 mmol) in chloroform (50 mL) was treated with N-bromosuccinimide (1.2 g, 6.7 mmol), stirred at ambient temperature for 20 minutes, concentrated to dryness, heated at 130° C. under nitrogen for 15 minutes and allowed to cool to ambient temperature. The residue was purified on silica gel eluting with ethyl acetate:formic acid:water:hexane (38:1:1:40, then 38:1:1:20 then 38:1:1:10) to provide the title compound as the less polar diastereomer.

Workup

  1. concentrationconcentrated to dryness
  2. temperatureheated at 130° C. under nitrogen for 15 minutes
  3. temperatureto cool to ambient temperature
  4. customThe residue was purified on silica gel eluting with ethyl acetate:formic acid:water:hexane (38:1:1:40

Sources & evidence

ORD record
ord-f3c9883cfd2c4383ab7d6994eb443fd9
Source dataset
uspto-grants-2003_10
Patent number
US06632418B2

Reaction notes

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