Iodoethane → 1-Ethyl-3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester

HRID 2264911Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:30](I)[CH3:31]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH2:30][CH3:31])[C:13]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 3-(2-fluoro-4-iodo-phenylamino)-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid ethyl ester (210 mg, 0.49 mmol), potassium carbonate (82 mg, 0.59 mmol) and ethyl iodide (44 μl, 0.54 mmol) in DMF was heated at 55° C. for 2 hours. The mixture was allowed to cool to ambient temperature then evaporated. The residue was partitioned between EtOAc (50 mL) and water (15 mL). The organic phase was separated, dried (Na2SO4), filtered and evaporated to give an oil. The oil was purified by flash column chromatography on silica (Si-PPC, pentane:EtOAc, gradient 100:0 to 40:60) to provide the title compound as a yellow solid (80 mg, 36%). LCMS (method B): RT=2.52 min, M+H+=454.

Workup

temperatureto cool to ambient temperature
customthen evaporated
customThe residue was partitioned between EtOAc (50 mL) and water (15 mL)
customThe organic phase was separated
dry with materialdried (Na2SO4)
filtrationfiltered
customevaporated
customto give an oil
customThe oil was purified by flash column chromatography on silica (Si-PPC, pentane:EtOAc, gradient 100:0 to 40:60)

Sources & evidence

ORD record: ord-ba6fda0ce0934012932f28cffdd10704
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855216B2

Reaction notes

Loading…