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

HRID 576254Notes

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

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

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

Sources & evidence

ORD record: ord-7d77e28985da44c1926b233fcb974b7f
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035047B2

Reaction notes

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