N-Iodosuccinimide → HCID 12083025, compound

HRID 1168500Notes

Reaction equation

HRID 1168500 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].[I:22]N1C(=O)CCC1=O>CN(C=O)C>[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([I:22])[CH:9]=2)[N:4]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 2776402Benzyl 2-(Hydroxymethyl)-1-Indolinecarboxylate

Product 1

HCID 12083025HCID 12083025, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution containing benzyl 2-(hydroxymethyl)-1-indolinecarboxylate (Preparation 6, 1.78 g), N-iodosuccinimide (2.83 g), and anhydrous DMF (12 mL) is stirred overnight at 60° C. in a foil-covered flask. This solution is cooled and concentrated to half volume with a stream of nitrogen. The resulting brown solution is partitioned between water (50 mL) and CH2Cl2 (150 mL). The organic phase is washed with brine, dried (Na2SO4), filtered, and concentrated to give a brown oil. The crude product is chromatographed eluting with 0-40% EtOAc in heptane (300 mL each 10%) to give 2.03 g (79%) of the title compound as a peach solid. Physical characteristics: M.p. 110-111° C.; HRMS (FAB) m/z 410.0270 (C17H16INO3+H). Anal. Found: C, 49.83; H, 3.95; N, 3.37.

Workup

  1. temperatureThis solution is cooled
  2. concentrationconcentrated to half volume with a stream of nitrogen
  3. customThe resulting brown solution is partitioned between water (50 mL) and CH2Cl2 (150 mL)
  4. washThe organic phase is washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil
  9. customThe crude product is chromatographed
  10. washeluting with 0-40% EtOAc in heptane (300 mL each 10%)

Sources & evidence

ORD record
ord-6d3878d2ff2d4878bed7de02de17e0d9
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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