Hydrogen Bromide → (5-iodo-2,3-dihydro-1H-indol-2-yl)methyl acetate

HRID 1168501Notes

Reaction equation

HRID 1168501 reaction equation
Br.[OH:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:13])[CH:10]=2)[N:5]1C(OCC1C=CC=CC=1)=O.[CH2:24](Cl)Cl.[CH3:27][OH:28]>C(O)(=O)C.C(N(CC)CC)C>[C:27]([O:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:13])[CH:10]=2)[NH:5]1)(=[O:28])[CH3:24]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 887MethanolHCID 6344DichloromethaneHCID 12083025HCID 12083025, compound

Product 1

HCID 12083026(5-iodo-2,3-dihydro-1H-indol-2-yl)methyl acetateYield 84%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8471TriethylamineSolvent

Procedure

A 30% wt solution containing HBr in acetic acid (25 mL) is added to a flask containing benzyl 2-(hydroxymethyl)-5-iodo-1-indolinecarboxylate (Preparation 8, 6.03 g). All of the solids are dissolved and the solution is concentrated to give a brown solid. The crude product is taken into CH2Cl2 with a small amount of methanol and triethylamine and purified by column chromatography eluting with heptane (250 mL), 20% EtOAc in heptane (500 mL), and 40% EtOAc in heptane to give 3.92 g (84%) of the title compound as a red solid. Physical characteristics: M.p. 64-66° C.; HRMS (FAB) m/z 318.0006 (C11H12INO2+H). Anal. Found: C, 41.91; H, 3.85; N, 4.35.

Workup

  1. additionis added to a flask
  2. dissolutionAll of the solids are dissolved
  3. concentrationthe solution is concentrated
  4. customto give a brown solid
  5. custompurified by column chromatography
  6. washeluting with heptane (250 mL), 20% EtOAc in heptane (500 mL), and 40% EtOAc in heptane

Sources & evidence

ORD record
ord-495fef92cac143db80b21c502bc7b149
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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