Imidazole → ethyl 7-bromo-3-(3-iodopropyl)-1H-indole-2-carboxylate

HRID 2095252Notes

Reaction equation

HRID 2095252 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18]O.[I:20]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][I:20]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 68943187ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate

Product 1

HCID 68936016ethyl 7-bromo-3-(3-iodopropyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of EXAMPLE 1B (1.116 g) in dichloromethane (30 mL) at 0° C. was added iodine (1.01 g), triphenyl phosphine (1.03 g) and imidazole (0.535 g). The mixture was stirred at 0° C. for 1 hour and treated with saturated NaHCO3 (50 mL). Stirring was continued for 30 minutes, and the organic layer was washed with a saturated aqueous Na2S2O3 (50 mL), water (20 mL), and brine (50 mL) and dried (Na2SO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel (with 0-20% ethyl acetate in hexanes.

Workup

  1. stirringStirring
  2. waitwas continued for 30 minutes
  3. washthe organic layer was washed with a saturated aqueous Na2S2O3 (50 mL), water (20 mL), and brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by column chromatography on silica gel (with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c7189dfa8087460a9f97986027d163b8
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

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